GB1167777A - Indole Derivatives - Google Patents
Indole DerivativesInfo
- Publication number
- GB1167777A GB1167777A GB3763967A GB3763967A GB1167777A GB 1167777 A GB1167777 A GB 1167777A GB 3763967 A GB3763967 A GB 3763967A GB 3763967 A GB3763967 A GB 3763967A GB 1167777 A GB1167777 A GB 1167777A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- chlorobenzoyl
- malonate
- chlorine
- butyl
- 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
1,167,777. lndole derivatives. MEROK & CO. Inc. 16 Aug., 1967 [23 Aug., 1966], No. 37639/67. Heading C2C. Novel indole derivatives of the general formula wherein X is a chlorine or bromine atom or a p-toluene-sulphonyloxy group and X<SP>1</SP> is a hydrogen, chlorine or bromine atom are prepared (a) when X is a chlorine or bromine atom and X<SP>1</SP> is a hydrogen atom, by refluxing di-t-butyl 1-p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole- 3-α-(bromo or chloro)malonate in a solvent until evolution of isobutylene ceases; (b) when X and X<SP>1</SP> are each a chlorine or bromine atom, by refluxing the malonate specified in (a) above in toluene in the presence of p-toluenesulphonic acid until one equivalent of isobutylene is collected, halogenating the resulting t-butyl 1- p - chlorobenzoyl - 2 - methyl - 5 - methoxy - indole- 3-α-(bromo or chloro)acetate with an ethereal solution of chlorine or bromine and heating the resulting t-butyl 1-p-chlorobenzoyl-2-methyl- 5 - methoxyindole - 3 - α α - di - (bromo or chloro)- acetate with p-toluenesulphonic acid in toluene; or (c) when X is a p-toluenesulphonyloxy group and X<SP>1</SP> is a hydrogen atom, by treatment of the malonate specified in (a) above with silver nitrate in aqueous acetone, followed by treatment of the resulting 1.p.chlorobenzoyl-2.methyl-5- methoxy-indole-3-α-hydroxyacetic acid with ptoluenesulphonylchloride. Di - t - butyl 1 - p - chlorobenzoyl - 2 - methyl- 5 - methoxyindole - 3 - α - (bromo or chloro)- malonate is prepared by condensing p-methoxyphenylhydrazine with 2-acetonylmalonic acid di-t-butyl ester, treating the resulting di-tbutyl 2 - methyl - 5 - methoxyindole - 3 - malonate with p-chlorobenzoyl chloride and sodium hydride and treating the resulting di-t-butyl 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole- 3-malonate with bromine or chlorine in a solvent. Indole derivatives of the above general formula may be reduced to give 1 -p-chlorobenzoyl - 2 - methyl - 5 - methoxy - 3 - indolylacetic acid, e.g. by means of hydrogen in the presence of a noble metal or Raney nickel catalyst, or hydrogen generated in situ.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA968566 | 1966-08-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1167777A true GB1167777A (en) | 1969-10-22 |
Family
ID=4142636
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3763967A Expired GB1167777A (en) | 1966-08-23 | 1967-08-16 | Indole Derivatives |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH505822A (en) |
DE (1) | DE1695452A1 (en) |
GB (1) | GB1167777A (en) |
NL (1) | NL6711390A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
EP0210660A2 (en) | 1985-07-31 | 1987-02-04 | Fuji Photo Film Co., Ltd. | Image forming process |
EP0772088A1 (en) | 1991-03-05 | 1997-05-07 | Fuji Photo Film Co., Ltd. | Heat-developable diffusion transfer color photographic material |
-
1967
- 1967-08-16 GB GB3763967A patent/GB1167777A/en not_active Expired
- 1967-08-18 NL NL6711390A patent/NL6711390A/xx unknown
- 1967-08-22 DE DE19671695452 patent/DE1695452A1/en active Pending
- 1967-08-23 CH CH1182267A patent/CH505822A/en not_active IP Right Cessation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0143424A2 (en) | 1983-11-25 | 1985-06-05 | Fuji Photo Film Co., Ltd. | Heat-developable light-sensitive materials |
EP0210660A2 (en) | 1985-07-31 | 1987-02-04 | Fuji Photo Film Co., Ltd. | Image forming process |
EP0772088A1 (en) | 1991-03-05 | 1997-05-07 | Fuji Photo Film Co., Ltd. | Heat-developable diffusion transfer color photographic material |
Also Published As
Publication number | Publication date |
---|---|
NL6711390A (en) | 1968-02-26 |
CH505822A (en) | 1971-04-15 |
DE1695452A1 (en) | 1971-07-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |