GB854632A - Manufacture of pyrazoles - Google Patents
Manufacture of pyrazolesInfo
- Publication number
- GB854632A GB854632A GB4671/57A GB467157A GB854632A GB 854632 A GB854632 A GB 854632A GB 4671/57 A GB4671/57 A GB 4671/57A GB 467157 A GB467157 A GB 467157A GB 854632 A GB854632 A GB 854632A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbethoxy
- group
- phenyl
- hydrazine
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003217 pyrazoles Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 5
- -1 mono-substituted hydrazine Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 abstract 1
- FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical compound NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001409 amidines Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002084 enol ethers Chemical class 0.000 abstract 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
The invention comprises 3-aminopyrazoles unsubstituted in the 1- and 5-positions, having in the 4-position a carboxyl group or functional derivative thereof and optionally substituted in the 2-position by an unsubstituted or substituted alkyl or aryl group; also salts of these; 3-amino-4-cyanopyrazol is however not claimed per se. The pyrazoles are made by condensing hydrazine or a mono-substituted hydrazine with a derivative of a -cyano-a -formyl-acetic acid functionally converted in the acid residue and also optionally in the aldehyde residue. The reaction between hydrazine itself and ethoxy-methylene-malodinitrile is excluded. The substituent in the 4-position of the product can be converted into a free carboxyl or any functional derivative thereof (including salts). The starting material can be a cyanacetic acid, ester, amide or amidine or a malonic dinitrile, substituted by a formyl group or enol ether, acetal or mercaptal thereof. The substituent in the hydrazine group can be alkyl, hydroxyalkyl, aryl or haloaryl. After-treatment of the 4-substituent can lead to an ester, halide, amide, thioamide or imino-ether group. The 3-amino group can be acylated, e.g. acetylated or benzoylated. The products can be converted into pyrazolo-pyrimidines as in Specification 835,918 and Specification 854,631. The carboxylic groups form salts with alkali and alkaline earth metals. The basic compounds form salts e.g. with hydrohalic, sulphuric, nitric, perchloric, phosphoric, formic, acetic, propionic, lactic, oxalic, succinic, malic, tartaric, citric, ascorbic, methanesulphonic, ethanesulphonic, isethionic, benzoic, salicylic, p-aminosalicylic, toluenesulphonic and naphthalenesulphonic acids. Examples show the preparation of the following 3-aminopyrazoles:-4-carbethoxy, 2-phenyl-4-carbethoxy, 2-phenyl-4-cyano, 2-phenyl-4-carbamyl, 2-isopropyl-4-carbethoxy, 2-isopropyl-4-carbamyl, 2-(p-chlorophenyl)-4-carbethoxy, 2-(b -hydroxyethyl)-4-carbethoxy, 2-(b -hydroxyethyl)-4-cyano, 2-(b -hydroxyethyl)-4-carbamyl and 2-phenyl-4-carboxy.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH854632X | 1956-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB854632A true GB854632A (en) | 1960-11-23 |
Family
ID=4542572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4671/57A Expired GB854632A (en) | 1956-02-10 | 1957-02-11 | Manufacture of pyrazoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB854632A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694484A (en) * | 1969-09-09 | 1972-09-26 | Ronald M Cresswell | Process of preparing 3-amino-2-cyano acrylamide |
| DE1795720A1 (en) * | 1966-07-14 | 1974-08-29 | Wellcome Found | PROCESS FOR THE PREPARATION OF 4AND / OR 4,6-DIHYDROXY-PYRAZOLO- (3,4) PYRIMIDINES |
| EP0053698A1 (en) * | 1980-12-05 | 1982-06-16 | BASF Aktiengesellschaft | 5-Amino-1-phenylpyrazole-4-carboxylic acids, process for their preparation, herbicides containing them and their use as herbicides |
| DE3325853A1 (en) * | 1983-03-21 | 1984-09-27 | Siegfried AG, Zofingen | Process for the preparation of allopurinol |
-
1957
- 1957-02-11 GB GB4671/57A patent/GB854632A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795720A1 (en) * | 1966-07-14 | 1974-08-29 | Wellcome Found | PROCESS FOR THE PREPARATION OF 4AND / OR 4,6-DIHYDROXY-PYRAZOLO- (3,4) PYRIMIDINES |
| US3694484A (en) * | 1969-09-09 | 1972-09-26 | Ronald M Cresswell | Process of preparing 3-amino-2-cyano acrylamide |
| EP0053698A1 (en) * | 1980-12-05 | 1982-06-16 | BASF Aktiengesellschaft | 5-Amino-1-phenylpyrazole-4-carboxylic acids, process for their preparation, herbicides containing them and their use as herbicides |
| DE3325853A1 (en) * | 1983-03-21 | 1984-09-27 | Siegfried AG, Zofingen | Process for the preparation of allopurinol |
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