GB635635A - Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes - Google Patents
Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenesInfo
- Publication number
- GB635635A GB635635A GB19141/47A GB1914147A GB635635A GB 635635 A GB635635 A GB 635635A GB 19141/47 A GB19141/47 A GB 19141/47A GB 1914147 A GB1914147 A GB 1914147A GB 635635 A GB635635 A GB 635635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- chloro
- methoxynaphthalene
- halogen
- alcohol
- 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
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 title 1
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- 238000002425 crystallisation Methods 0.000 abstract 4
- 230000008025 crystallization Effects 0.000 abstract 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910017604 nitric acid Inorganic materials 0.000 abstract 3
- IYPXDSDLYHJSIH-UHFFFAOYSA-N 1-chloro-2-methoxy-6-nitronaphthalene Chemical compound [N+](=O)([O-])C=1C=C2C=CC(=C(C2=CC=1)Cl)OC IYPXDSDLYHJSIH-UHFFFAOYSA-N 0.000 abstract 2
- RPURXCRKUMBNJK-UHFFFAOYSA-N 1-chloro-2-methoxynaphthalene Chemical compound C1=CC=CC2=C(Cl)C(OC)=CC=C21 RPURXCRKUMBNJK-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 238000006396 nitration reaction Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- IEYASRWFLANSJG-UHFFFAOYSA-N 1-chloro-2-ethoxy-8-nitronaphthalene Chemical compound [N+](=O)([O-])C=1C=CC=C2C=CC(=C(C=12)Cl)OCC IEYASRWFLANSJG-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-ethoxy compound Chemical class 0.000 abstract 1
- GBDHUPNYWPOQFZ-UHFFFAOYSA-N 5-chloro-6-methoxynaphthalen-2-amine Chemical compound NC=1C=C2C=CC(=C(C2=CC=1)Cl)OC GBDHUPNYWPOQFZ-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mononitro - 1 - halogen - 2 - alkoxynaphthalenes are prepared by the treatment of a 1-halogen-2-alkoxynaphthalene with a nitrating agent consisting of nitric acid alone, and isolating at least one of the resulting isomers. The halogen is e.g. chlorine and the alkoxy group e.g. methoxy or ethoxy. For the nitration, nitric acid is used alone or mixed with an inert organic solvent, e.g. chlorobenzene. Temperatures in the range 10-80 DEG C., particularly 40-60 DEG C., are preferred. The product consists of 6-, 8-, and 4-nitro-2-alkoxy-1-halogen-naphthalenes. The 6-nitro compounds (particularly when the alkoxy group is methoxy) may be isolated by making use of their insolubility in boiling alcohol; with higher alkoxy groups, crystallization alternately from alcohol and carbon disulphide may be necessary. The compounds may be separated by distillation, preferably in vacuo; further purification may be effected by crystallization from carbon disulphide. In the examples: (1) powdered 1-chloro-2-methoxynaphthalene is added to nitric acid (62 per cent), the temperature being maintained at e.g. 40 DEG C. by cooling, to yield on dilution with water a crude product which is extracted with boiling ethanol to leave a residue of 6-nitro-1-chloro-2-methoxynaphthalene. The latter is reduced in alcohol with iron and a little acid to give 6-amino-1-chloro-2-methoxynaphthalene. In example (2) a solution of 1 - chloro - 2 - methoxynaphthalene in chlorobenzene is nitrated at 40-60 DEG C. and 6 - nitro - 1 - chloro - 2 - methoxynaphthalene isolated from the product. The 2-ethoxy compound is prepared in a similar way, isolated by crystallization, and reduced to the 6-amino compound. Example (3) is similar to example (2), but in addition to the isolation of the 6-nitro derivative, the more alcohol-soluble isomers are fractionally distilled in vacuo, and after a crystallization procedure, the 4-nitro and 8-nitro isomers are also obtained. The latter 8-nitro isomer is reduced to the 8-amino compound; the 8-nitro-1-chloro-2-ethoxy-naphthalene may be prepared in a similar manner. The Specification as open to inspection under Sect. 91 refers to the use of nitration agents in general. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH635635X | 1946-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB635635A true GB635635A (en) | 1950-04-12 |
Family
ID=4525076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19141/47A Expired GB635635A (en) | 1946-07-26 | 1947-07-17 | Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB635635A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108604A1 (en) * | 1982-11-05 | 1984-05-16 | Uniroyal, Inc. | Preparation of mono-nitro aromatic compounds |
| WO1985002615A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Nitration of phthalic acid and phthalic anhydride using nitric acid |
| WO1985002612A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Method for making n-substituted nitrophthalimides |
| WO1985002613A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Destruction of dnpi in an all nitric acid nitration process |
| US4902809A (en) * | 1983-12-08 | 1990-02-20 | General Electric Company | Method for making N-substituted nitrophthalimides |
-
1947
- 1947-07-17 GB GB19141/47A patent/GB635635A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108604A1 (en) * | 1982-11-05 | 1984-05-16 | Uniroyal, Inc. | Preparation of mono-nitro aromatic compounds |
| WO1985002615A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Nitration of phthalic acid and phthalic anhydride using nitric acid |
| WO1985002612A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Method for making n-substituted nitrophthalimides |
| WO1985002613A1 (en) * | 1983-12-08 | 1985-06-20 | General Electric Company | Destruction of dnpi in an all nitric acid nitration process |
| US4902809A (en) * | 1983-12-08 | 1990-02-20 | General Electric Company | Method for making N-substituted nitrophthalimides |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Smith et al. | The electronic character of the azido group attached to benzene rings | |
| Utne et al. | Synthesis of 2-and 4-fluoroestradiol | |
| GB635635A (en) | Manufacture of substituted mononitronaphthalenes and substituted monoaminonaphthalenes | |
| Cope et al. | Amine Oxides. II. Conversion to N, N-Dialkylhydroxylamines1 | |
| US2411670A (en) | Halogen-b-htdeoxy-qtjinaldines | |
| US2273922A (en) | Fluorine-containing compounds of the naphthalene series | |
| US2007234A (en) | xx x x xx | |
| Kirby et al. | 1, 2, 3-Benzothiadiazoles. Part I. A simplified synthesis of 1, 2, 3-benzothiadiazoles | |
| Mizuno et al. | Benzothiazoles. III Synthesis of 2-Methylbenzothiazoles with Electron-attracting Groups | |
| Dewar et al. | 182. Electrophilic substitution. Part IX. The anomalous nitrations of quinoline | |
| Ross et al. | Tetrakis-(trifluoromethyl)-biphenyls | |
| US2019837A (en) | Chloro-benzoylamino-anthraquinone | |
| Suzuki et al. | Nitration of 9, 10-Dialkylphenanthrenes. Side-chain Nitrooxylation in Competition with Side-chain Nitration | |
| US3830854A (en) | Substituted 5,8-dimethyl-5,6,7,8-tetrahydro-1-naphthols | |
| Buu-Hoï | 166. The chemistry of carcinogenic nitrogen compounds. New derivatives of the angular benzacridines and of some related nuclei | |
| US2140480A (en) | 3-keto-d-pentonic acid lactone and process for the manufacture of same | |
| Ternay Jr et al. | Borohydride reduction of thioxanthone sulfoxide. Base-induced dehydration of thioxanthenol sulfoxide | |
| Sawicki et al. | Nitrogen Derivatives of Dibenzoselenophene1 | |
| Grotta et al. | Some hydroxylated derivatives of chlorpromazine | |
| US1659358A (en) | A cobposatiost | |
| Bassilios et al. | Di‐and tri‐nitro derivatives of 1‐chloronaphthalene | |
| Jones et al. | 1, 2-Diphenyl-3-nitrocyclopropene or 2, 3-Diphenyl-2-cyclopropenyl Nitrite1 | |
| US2032519A (en) | Chloro-benzoylamino-anthraquinones | |
| Adams et al. | Quinone imides. XVIII. p-Quinonedipivalimides and their reactions | |
| Rabindran et al. | Thiophenes and thiapyrans: Part XI. A new route to polycyclic thiophenes |