GB1197251A - N-Phenyl p-Chlorobenzamide Derivatives and their Conversion to Indolyl Acetic Acid Derivatives - Google Patents
N-Phenyl p-Chlorobenzamide Derivatives and their Conversion to Indolyl Acetic Acid DerivativesInfo
- Publication number
- GB1197251A GB1197251A GB1044968A GB1044968A GB1197251A GB 1197251 A GB1197251 A GB 1197251A GB 1044968 A GB1044968 A GB 1044968A GB 1044968 A GB1044968 A GB 1044968A GB 1197251 A GB1197251 A GB 1197251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- dimethylamino
- chlorobenzamido
- phenyl
- acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,197,251. N-Substituted-p-chlorobenzamides- and their conversion to indolyl acetic acids. MERCK & CO. Inc. 4 March, 1968 [9 March, 1967], No. 10449/68. Heading C2C. Novel N-phenyl-p-chlorobenzamide derivatives of the Formulµ II and III respectively wherein R is a methoxy or dimethylamino group, R<SP>1</SP> is a hydrogen atom or a C 1-5 alkyl or an (C 1-5 alkyl) group, Hal is a chlorine bromine or iodine atom and R‹ is a p-chlorobenzoyl group; are obtained either by (a) condensing p-chlorobenzoyl chloride with 2- amino-5-methoxy or dimethylamino-cinnomic acid esters and reacting the 2-(p-chlorobenzamido)-5 methoxy or dimethylamino cinamic acid esters produced with nitroethane, or (b) reducing 2-nitro-5-methoxy or dimethylamino-benzaldehyde to 2-amino-5-methoxy of dimethylaminobenzaldehyde, acylating this with p-chlorobenzoyl chloride, treating the 2-(p-chlorobenzamido)-5-Methoxy of dimethylamino-benzaldehyde produced with nitroethane to give 1-(2<SP>1</SP>-pchlorobenzamido-5-methoxy or dimethylaminophenyl)-2-nitropropene, reacting this with a malonic acid esters and alkali-metal alkoxides, and decarboxylating the 2-alkali metal-2-carboxy - 3 - (2<SP>1</SP> - p - chlorobenzamido - 5<SP>1 </SP>- methoxy or dimethylamino phenyl)-4-nitrovaleric acids so produced after hydrolysis of the corresponding esters, and if desired, halogenating the compounds of Formula I so produced to the corresponding compounds of Formula II. Indolylacetic acid derivatives of the Formula I may be obtained from the above compounds of Formulµ II or III by any of four multistage processes. These involve (a) treating the compounds of Formula III with aqueous bases to give 3-(2<SP>1</SP>-p-chlorobenzamido-5<SP>1</SP>-methoxy or dimethylamino-phenyl)- 4 - nitropent - 3 - enoic acid which can be cyclized by reduction, (b) treating compounds of Formula III with alkoxides to give 1-p-chlorobenzoyl-2-methyl-2- nitro.5-methoxy or dimethylamino-3-indolinyl acetic acid and removing the elements of nitrous acid therefrom, (c) reducing carboxylic acids of Formula II to 3-(2<SP>1</SP>-p-chlorobenzamido-5<SP>1</SP>- methoxy of dimethylamino phenyl)-4-amino valeric acid chlorinating this to 3-(2<SP>1</SP>-p-chlorobenzamido-5<SP>1</SP>-methoxy or dimethylamino phenyl-4- chloramino valeric acid, dehydrochlorinating this to 3-(2<SP>1</SP>-p-chlorobenzamido-5<SP>1</SP>-methoxy or dimethylamino phenyl) levulinic acid ketimine which is then cyclized, or (D) hydrolysing compounds of Formula II to 3-(2<SP>1</SP>-p-chlorobenzamido-5-methoxy or dimethylamino) phenyl levulinic acid and cyclizing this.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA984830 | 1967-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1197251A true GB1197251A (en) | 1970-07-01 |
Family
ID=4142841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1044968A Expired GB1197251A (en) | 1967-03-09 | 1968-03-04 | N-Phenyl p-Chlorobenzamide Derivatives and their Conversion to Indolyl Acetic Acid Derivatives |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH494224A (en) |
| DE (1) | DE1668479A1 (en) |
| FR (1) | FR1555403A (en) |
| GB (1) | GB1197251A (en) |
| NL (1) | NL6802551A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112225728A (en) * | 2020-08-18 | 2021-01-15 | 四川农业大学 | Multi-substituted benzamide compound and preparation method and application thereof |
| CN115015437A (en) * | 2022-07-04 | 2022-09-06 | 贵州茅台酒股份有限公司 | Derivatization-based high-coverage analysis method for carboxyl compounds in white spirit |
-
1968
- 1968-02-22 NL NL6802551A patent/NL6802551A/xx unknown
- 1968-03-04 GB GB1044968A patent/GB1197251A/en not_active Expired
- 1968-03-07 DE DE19681668479 patent/DE1668479A1/en active Pending
- 1968-03-08 FR FR1555403D patent/FR1555403A/fr not_active Expired
- 1968-03-08 CH CH346068A patent/CH494224A/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112225728A (en) * | 2020-08-18 | 2021-01-15 | 四川农业大学 | Multi-substituted benzamide compound and preparation method and application thereof |
| CN115015437A (en) * | 2022-07-04 | 2022-09-06 | 贵州茅台酒股份有限公司 | Derivatization-based high-coverage analysis method for carboxyl compounds in white spirit |
| CN115015437B (en) * | 2022-07-04 | 2023-04-21 | 贵州茅台酒股份有限公司 | High coverage analysis method for carboxyl compounds in white spirit based on derivatization |
Also Published As
| Publication number | Publication date |
|---|---|
| CH494224A (en) | 1970-07-31 |
| NL6802551A (en) | 1968-09-10 |
| DE1668479A1 (en) | 1971-10-28 |
| FR1555403A (en) | 1969-01-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |