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WO2015115339A1 - Procédé de production d'un composé pyridine - Google Patents

Procédé de production d'un composé pyridine Download PDF

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Publication number
WO2015115339A1
WO2015115339A1 PCT/JP2015/051940 JP2015051940W WO2015115339A1 WO 2015115339 A1 WO2015115339 A1 WO 2015115339A1 JP 2015051940 W JP2015051940 W JP 2015051940W WO 2015115339 A1 WO2015115339 A1 WO 2015115339A1
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Prior art keywords
group
cyano
formula
compound
compound represented
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PCT/JP2015/051940
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English (en)
Japanese (ja)
Inventor
孝行 若松
優太 長島
理香 井本
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Publication of WO2015115339A1 publication Critical patent/WO2015115339A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles

Definitions

  • the present invention relates to a method for producing a pyridine compound.
  • X 1 represents a halogen atom
  • R 1 , R 2 and R 3 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkoxy group, an alkyl group or an aryl group
  • the alkyl group may have at least one group selected from a halogen atom, a cyano group, a nitro group, an alkoxy group, and an aryl group
  • the aryl group herein includes a halogen atom, a cyano group, a nitro group, (It may have at least one group selected from a group, an alkoxy group, and a haloalkoxy group.) Is known to be an intermediate useful as an intermediate for agricultural chemicals or pharmaceuticals.
  • Example 169 of WO 1995/026966 describes a method for producing 3-chloro-2-cyanopyridine in which phosphorus pentachloride is added to a phosphorus oxychloride solution of 3-hydroxypicolinamide and heated to reflux. was only about 15%.
  • the present invention relates to formula (4) (Wherein R 1 , R 2 and R 3 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkoxy group, an alkyl group or an aryl group, and the alkyl group represents a halogen atom, It may have at least one group selected from a cyano group, a nitro group, an alkoxy group, and an aryl group, and the aryl group in this application is a halogen atom, a cyano group, a nitro group, an alkoxy group, or a haloalkoxy group.
  • a compound represented by the formula (3) is reacted with cyanide and ammonia.
  • a step of obtaining a compound represented by formula (2) reacting a compound represented by formula (3) with an oxidizing agent to produce a compound represented by formula (2) (Wherein R 1 , R 2 and R 3 represent the same meaning as described above.)
  • a compound represented by formula (1) and a step of reacting the compound represented by formula (2) with a halogenating agent.
  • X 1 represents a halogen atom
  • R 1 , R 2 and R 3 have the same meaning as described above.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom or a chlorine atom.
  • alkyl group examples include alkyl groups having 1 to 6 carbon atoms such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group.
  • alkoxy group examples include alkoxy having 1 to 6 carbon atoms such as methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, and hexyloxy group.
  • aryl group examples include aryl groups having 6 to 10 carbon atoms such as a phenyl group, a tolyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • aryl group is used to mean an aromatic hydrocarbon group that may have at least one group selected from a halogen atom, a cyano group, a nitro group, an alkoxy group, and a haloalkoxy group. .
  • Examples of the aryl group having a substituent are 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl.
  • alkyl group having a halogen atom examples include haloalkyl groups having 1 to 6 carbon atoms such as a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, and a pentafluoroethyl group, and preferably a perfluorocarbon group having 1 to 6 carbon atoms.
  • Examples of the alkyl group having a cyano group include a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, a 1-cyanopropyl group, a 2-cyanopropyl group, and a 3-cyanopropyl group, preferably a cyanomethyl group.
  • Examples of the alkyl group having a nitro group include a nitromethyl group, a 1-nitroethyl group, a 2-nitroethyl group, a 1-nitropropyl group, a 2-nitropropyl group, and a 3-nitropropyl group, and a nitromethyl group is preferable.
  • alkyl group having an alkoxy group examples include methoxymethyl group, ethoxymethyl group, benzyloxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-methoxypropyl group, 2-methoxypropyl group and 3-methoxypropyl.
  • a methoxymethyl group and a benzyloxymethyl group are preferable.
  • alkyl group having an aryl group examples include phenylmethyl group, (2-fluorophenyl) methyl group, (3-fluorophenyl) methyl group, (4-fluorophenyl) methyl group, (2-chlorophenyl) methyl group, (3 -Chlorophenyl) methyl group, (4-chlorophenyl) methyl group, (2-bromophenyl) methyl group, (3-bromophenyl) methyl group, (4-bromophenyl) methyl group, (2-iodophenyl) methyl group, (3-iodophenylmethyl) group, (4-iodophenyl) methyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group and 3-phenylpropyl group.
  • R 1 , R 2 and R 3 are preferably the same group.
  • Each of R 1 , R 2 and R 3 is preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a haloalkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom.
  • halogenating agents include phosphorus oxyhalides such as phosphorus oxychloride and phosphorus oxybromide; phosphorus halides such as phosphorus trichloride, phosphorus pentachloride and phosphorus tribromide; methanesulfonyl chloride, p-toluenesulfonyl chloride and the like. Sulfonyl chloride; thionyl chloride; phosgene and the like. Phosphorus halide is preferable, and phosphorus pentachloride is more preferable.
  • the amount of the halogenating agent to be used is generally 1 to 10 mol, preferably 1 to 3 mol, per 1 mol of compound (2).
  • the reaction of the compound (2) and the halogenating agent is usually carried out by mixing the compound (2) and the halogenating agent.
  • the additive include bases such as triethylamine and diisopropylethylamine; amide compounds such as N, N′-dimethylformamide and N, N′-dimethylacetamide, preferably amide compounds, more preferably N, N ′. -Dimethylformamide.
  • the amount of the additive used is usually 0.01 to 10 mol with respect to 1 mol of the compound (2).
  • the reaction between the compound (2) and the halogenating agent is preferably performed in a nitrogen atmosphere.
  • the reaction of the compound (2) and the halogenating agent may be performed in a solvent.
  • Solvents include aromatic hydrocarbon solvents such as benzene, toluene, chlorobenzene, nitrobenzene and xylene; halogenated hydrocarbon solvents such as chloroform and dichloromethane; nitrile solvents such as acetonitrile and propylnitrile; sulfoxide solvents such as dimethyl sulfoxide; and these The mixed solvent is mentioned.
  • An aromatic hydrocarbon solvent is preferable, and toluene is more preferable.
  • the amount of the solvent to be used is generally 0.1-100 parts by weight, preferably 0.1-7 parts by weight, relative to 1 part by weight of compound (2).
  • the reaction temperature is usually 50 to 150 ° C.
  • the reaction time is usually 0.1 to 100 hours, preferably 0.1 to 24 hours.
  • a reaction mixture containing compound (1) is obtained by reacting compound (2) with a halogenating agent.
  • the compound (1) can be isolated by, for example, concentrating the obtained reaction compound.
  • the isolated compound (1) may be purified by ordinary purification means such as distillation, column chromatography, recrystallization and the like.
  • oxidizing agent examples include halogens such as chlorine, bromine and iodine; hydrogen peroxide; peroxides such as peracetic acid, persulfuric acid, m-chloroperbenzoic acid and tert-butyl hydroperoxide; sodium hypochlorite, hypochlorous acid Hypochlorites such as potassium chlorate; Chlorites such as sodium chlorite and potassium chlorite; Chlorates such as sodium chlorate and potassium chlorate; Sodium perchlorate and potassium perchlorate Perchlorates; hypochlorous acid; chlorous acid; chloric acid and perchloric acid. Halogen or hydrogen peroxide is preferred, and chlorine, bromine or hydrogen peroxide is more preferred.
  • the amount of the oxidizing agent to be used is generally 1 to 10 mol, preferably 1 to 3 mol, per 1 mol of compound (3).
  • Reaction of a compound (3) and an oxidizing agent is normally implemented by mixing a compound (3) and an oxidizing agent.
  • the reaction is preferably carried out by adding an oxidizing agent to the compound (3).
  • the reaction between the compound (3) and the oxidizing agent is preferably performed in a nitrogen atmosphere.
  • the reaction between the compound (3) and the oxidizing agent is usually performed in the presence of a solvent.
  • Solvents include water; aromatic hydrocarbon solvents such as chlorobenzene; halogen-containing hydrocarbon solvents such as chloroform and dichloromethane; alcohol solvents such as methanol, ethanol and butanol; nitrile solvents such as acetonitrile and propylnitrile; heteroaromatics such as pyridine. Group solvents; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; and a mixed solvent thereof, preferably water.
  • the amount of the solvent used is usually 0.1 to 100 parts by weight per 1 part by weight of the compound (3).
  • the reaction is usually performed in the presence of an acid.
  • the acid include organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid and 4-toluenesulfonic acid; inorganic acids such as hydrochloric acid and sulfuric acid: ammonium chloride and the like. An inorganic acid is preferable, and hydrochloric acid is more preferable.
  • the amount of the acid to be used is generally 0.01-100 mol, preferably 0.01-1 mol, per 1 mol of compound (3).
  • the acid may be a mixture of an acid and a solvent. In the case of a mixture of an acid and a solvent, the concentration of the acid is usually 0.01 to 13 N, preferably 0.01 to 3 N.
  • the reaction temperature may be not less than the melting point of the solvent and not more than the boiling point, and is usually 0 to 100 ° C.
  • the temperature is preferably 0 to 90 ° C, more preferably 0 to 80 ° C.
  • the reaction time is usually 0.1 to 100 hours, preferably 10 hours or less.
  • the reaction of compound (4), cyanide and ammonia can be carried out by mixing compound (4), cyanide and ammonia.
  • the reaction is preferably carried out by adding ammonia to the mixture of cyanide and compound (4).
  • the reaction may be performed in the presence of a phase transfer catalyst, an acid, a dehydrating agent and / or a solvent, and is preferably performed in the presence of a solvent.
  • a catalyst, an acid, a dehydrating agent and / or a solvent may be added to the reaction system depending on the progress of the reaction.
  • Examples of the cyanide include alkali metal cyanides such as sodium cyanide and potassium cyanide: zinc cyanide, copper cyanide, hydrogen cyanide, etc., preferably alkali metal cyanide or hydrogen cyanide, more preferably sodium cyanide or hydrogen cyanide. It is.
  • a commercially available cyanide may be used, or a cyanide prepared by a known method may be used. Cyanide diluted in a solvent may be used. The amount of cyanide used is usually 1 to 10 moles per mole of compound (4).
  • Ammonia may be used in the form of gas or liquid. Commercially available ammonia may be used as it is, or ammonia produced according to a known method may be used.
  • a mixture of ammonia and a solvent may be used.
  • ammonia generated in the system from an ammonium salt such as ammonium chloride can also be used.
  • the amount of ammonia used is usually 1 to 10 moles per mole of compound (4).
  • phase transfer catalyst examples include quaternary ammonium salts such as tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, and benzyltributylammonium bromide; quaternary phosphonium salts such as heptyltriphenylphosphonium bromide and tetraphenylphosphonium bromide. It is done.
  • the amount of the phase transfer catalyst to be used is generally 0.01 to 10 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound (4).
  • Examples of the acid include organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid; ammonium chloride, and preferably acetic acid.
  • the amount of the acid used is usually 1 to 10 moles, preferably 1 to 3 moles per mole of cyanide.
  • Examples of the dehydrating agent include sodium sulfate, magnesium sulfate, magnesium oxide, calcium oxide, silica gel, molecular sieve and the like.
  • Solvents include water; aromatic hydrocarbon solvents such as benzene, chlorobenzene and toluene; halogenated hydrocarbon solvents such as chloroform and dichloromethane; alcohol solvents such as methanol, ethanol and butanol; 1,2-dimethoxyethane, diethylene glycol dimethyl ether, Ether solvents such as polyethylene glycol, tetrahydrofuran and dioxane; nitrile solvents such as acetonitrile and propyl nitrile; heteroaromatic solvents such as pyridine; sulfoxide solvents such as dimethyl sulfoxide; N, N-dimethylformamide, N, N-dimethylacetamide, N -Amide solvents such as methylpyrrolidone; organic acid solvents such as formic acid and acetic acid; and mixed solvents thereof.
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene and toluene
  • the solvent is preferably an alcohol solvent, more preferably methanol.
  • the amount of the solvent to be used is generally 0.1-100 parts by weight, preferably 0.1-2 parts by weight, relative to 1 part by weight of compound (4).
  • the reaction of compound (4), cyanide and ammonia is preferably carried out in a nitrogen atmosphere.
  • the reaction temperature is usually 0 to 100 ° C., preferably 0 to 80 ° C., more preferably 0 to 70 ° C.
  • the reaction time is usually 0.1 to 100 hours.
  • a reaction mixture containing compound (3) is obtained by the reaction of compound (4), cyanide and ammonia.
  • the compound (3) can be isolated by, for example, concentrating the obtained reaction compound.
  • Example 1 Under a nitrogen atmosphere, at room temperature, 28 g of sodium cyanide and 79.03 g of methanol were charged into a four-necked flask and cooled in an ice bath. A mixed solution of 50 g of furfural and 38 g of acetic acid was added dropwise over 2.5 hours. The resulting mixture was stirred for 1 hour in an ice bath, and 63 g of magnesium sulfate was added.
  • Example 3 At room temperature, 5.0 g of 1N hydrochloric acid and 1.0 g (6.31 mmol) of hydrochloride of ⁇ -amino-2-furanacetonitrile were charged into a three-necked flask.
  • the yield of 2-cyano-3-hydroxypyridine was 62% based on the hydrochloride salt of ⁇ -amino-2-furanacetonitrile.
  • Example 4 At room temperature, 0.46 g of 2-cyano-3-hydroxypyridine was charged into a three-necked flask. Under a nitrogen atmosphere, 3.0 ml of toluene and 1.31 g of phosphorus pentachloride were added, and the mixture was refluxed at a bath temperature of 120 ° C. for 10 hours. The mixture was allowed to cool to 70 ° C., water was added for liquid separation, and the aqueous layer was further extracted with toluene.
  • the pyridine compound represented by the formula (1) useful as an intermediate for agricultural chemicals or medicines can be obtained by the production method of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

La présente invention concerne un composé pyridine représenté par la formule (1) (dans laquelle R1, R2 et R3 représentent indépendamment un atome d'hydrogène, un atome d'halogène, un groupe cyano, un groupe nitro, un groupe alcoxy, un groupe alkyle, un groupe aryle ou analogues) qui peut être produit en faisant réagir un composé représenté par la formule (4) avec du cyanure et de l'ammoniac afin de produire un composé représenté par la formule (3), puis en faisant réagir le composé représenté par la formule (3) avec un agent oxydant afin de produire un composé représenté par la formule (2), et en faisant ensuite réagir le composé représenté par la formule (2) avec un agent halogénant.
PCT/JP2015/051940 2014-01-30 2015-01-19 Procédé de production d'un composé pyridine Ceased WO2015115339A1 (fr)

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JP2014015237 2014-01-30
JP2014-015237 2014-01-30

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111170935A (zh) * 2020-01-06 2020-05-19 上海海洋大学 3-羟基吡啶及利用糠醛制备3-羟基吡啶的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09511738A (ja) * 1994-04-01 1997-11-25 マイクロサイド・ファーマシューティカルズ・インコーポレーテッド セファロスポリン抗生物質
JP2013514315A (ja) * 2009-12-16 2013-04-25 エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト １，７−ジアザカルバゾール及び癌の治療におけるその使用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09511738A (ja) * 1994-04-01 1997-11-25 マイクロサイド・ファーマシューティカルズ・インコーポレーテッド セファロスポリン抗生物質
JP2013514315A (ja) * 2009-12-16 2013-04-25 エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト １，７−ジアザカルバゾール及び癌の治療におけるその使用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CLAUSON-KAAS, NIELS ET AL.: "Preparation of Derivatives of 3-Hydroxypicolinic Acid from Furfural", ACTA CHEMICA SCANDINAVICA, vol. 19, no. 5, 1965, pages 1147 - 1152 *
LAROCK, RICHARD C., COMPREHENSIVE ORGANIC TRANSFORMATIONS A GUIDE TO FUNCTIONAL GROUP PREPARATIONS, 1999, pages 703 *
O'SHEA, PAUL D. ET AL.: "Practical Synthesis of a Potent Bradykinin B1 Antagonist via Enantioselective Hydrogenation of a Pyridyl N- Acyl Enamide", J. ORG. CHEM., vol. 74, no. 12, 2009, pages 4547 - 4553, XP055215031 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111170935A (zh) * 2020-01-06 2020-05-19 上海海洋大学 3-羟基吡啶及利用糠醛制备3-羟基吡啶的方法
CN111170935B (zh) * 2020-01-06 2023-02-17 上海海洋大学 3-羟基吡啶及利用糠醛制备3-羟基吡啶的方法

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