GB600640A - Process for the manufacture of 5:4-disubstituted diphenylamine carboxylic acids - Google Patents
Process for the manufacture of 5:4-disubstituted diphenylamine carboxylic acidsInfo
- Publication number
- GB600640A GB600640A GB2646545A GB2646545A GB600640A GB 600640 A GB600640 A GB 600640A GB 2646545 A GB2646545 A GB 2646545A GB 2646545 A GB2646545 A GB 2646545A GB 600640 A GB600640 A GB 600640A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acid
- chloro
- nitro
- amino
- 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
- -1 5:4-disubstituted diphenylamine carboxylic acids Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000001184 potassium carbonate Substances 0.000 abstract 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 3
- 239000005711 Benzoic acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- FNORUNUDZNWQFF-UHFFFAOYSA-N 2,6-dimethyl-4-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1O FNORUNUDZNWQFF-UHFFFAOYSA-N 0.000 abstract 1
- CEXGTXNIIFSPSF-UHFFFAOYSA-N 2-Bromo-4-nitrobenzoic acid Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C=C1Br CEXGTXNIIFSPSF-UHFFFAOYSA-N 0.000 abstract 1
- SLOIKSLFBFEJHI-UHFFFAOYSA-N 2-chloro-4-(diethylamino)benzoic acid Chemical compound CCN(CC)C1=CC=C(C(O)=O)C(Cl)=C1 SLOIKSLFBFEJHI-UHFFFAOYSA-N 0.000 abstract 1
- TZXJLFBEXYSTJG-UHFFFAOYSA-N 4-acetamido-2-chlorobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C(Cl)=C1 TZXJLFBEXYSTJG-UHFFFAOYSA-N 0.000 abstract 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 abstract 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 238000005695 dehalogenation reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- RFOMKRIDPCCWRA-UHFFFAOYSA-M potassium;2-chloro-4-nitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1Cl RFOMKRIDPCCWRA-UHFFFAOYSA-M 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Abstract
5 : 41 - disubstituted - diphenylamine - 2 - carboxylic acids of the general formula: <FORM:0600640/IV(b)/1> in which R1 is a nitro group, an acylamino group or a mono- or di-alkyl-amino group and R1 is an amino group, an acylamino group or a substituted amino group are obtained by heating a 2-halogeno-benzoic acid containing the group R1 in the para-position to the carboxylic group or an alkali metal salt thereof, e.g. 4 - nitro - 2 - chlor and 4 - nitro - 2 - bromo benzoic acids, 4-acetylamino-2-chloro and 4 - diethylamino - 2 - chloro - benzoic acid, in an inert organic diluent in which said acid or salt is at least slightly soluble, e.g. a normally liquid alkanol or cycloalkanol having four to seven carbon atoms in the molecule, with an aniline containing the group R2 in the para position, e.g. p-phenylene diamine, a mono-acylated paraphenylene diamine or one in which the group in the para position has the general formula -NR5R6 in which R5 is hydrogen, an alkyl or an acyl group and R6 in an alkyl or an acyl group, at a temperature, e.g. 75-120 DEG C. below that at which substantial dehalogenation of the 2-halogeno benzoic acid occurs in the presence of an acid accepter, e.g. an alkali metal carbonate and a source of copper. In examples: (1) potassium 2-chloro-4-nitrobenzoate, potassium carbonate, copper powder and p-aminodimethyl aniline in amyl alcohol are heated at 120 DEG C. to produce 41-dimethyl-amino-5-nitrodiphenylamine-2-carboxylic acid; (2) 4-acetamido-2-chloro-benzoic acid, p-phenylene diamine, potassium carbonate, copper powder and amyl alcohol are heated at 110 DEG C. to produce p 5-acetamido-41-amino-diphenylamine-2-carboxylic acid; (3) 4-acetamido-2-chlorobenzine acid, p-acetamido aniline, potassium carbonate, copper powder and amyl alcohol are heated at 145-150 DEG C. to give a product identical with that of (2); (4) 2-chloro-4-nitro-benzoic acid, potasium carbonate, p-phenylene diamine, copper and amyl alcohol are heated at 75-100 DEG C. to produce 41-amino-5-nitro diphenylamine-2-carboxylic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB600640A true GB600640A (en) | 1948-04-14 |
Family
ID=1740055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2646545A Expired GB600640A (en) | 1945-10-10 | Process for the manufacture of 5:4-disubstituted diphenylamine carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB600640A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0282749A1 (en) * | 1987-02-26 | 1988-09-21 | Henkel Kommanditgesellschaft auf Aktien | Hair dyeing compositions containing direct nitrodiphenylamine derivatives |
-
1945
- 1945-10-10 GB GB2646545A patent/GB600640A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0282749A1 (en) * | 1987-02-26 | 1988-09-21 | Henkel Kommanditgesellschaft auf Aktien | Hair dyeing compositions containing direct nitrodiphenylamine derivatives |
| US4832697A (en) * | 1987-02-26 | 1989-05-23 | Henkel Kommanditgesellschaft Auf Aktien | Hair dye preparations containing substantive nitrodiphenylamine derivatives |
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