GB1161637A - Indole Derivatives - Google Patents

Indole Derivatives

Info

Publication number
GB1161637A
GB1161637A GB3764267A GB3764267A GB1161637A GB 1161637 A GB1161637 A GB 1161637A GB 3764267 A GB3764267 A GB 3764267A GB 3764267 A GB3764267 A GB 3764267A GB 1161637 A GB1161637 A GB 1161637A
Authority
GB
United Kingdom
Prior art keywords
general formula
indole
resulting
lutidine
treatment
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
Application number
GB3764267A
Inventor
John Martin Chemerda
Meyer Sletzinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1161637A publication Critical patent/GB1161637A/en
Expired legal-status Critical Current

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)

Abstract

1,161,637. Indole derivatives. MERCK & CO. Inc. 16 Aug., 1967 [25 Aug., 1966], No. 37642/67. Heading C2C. Indole derivatives of the general formula wherein R is a methoxy or dimethylamino group, are prepared by dissolving a 2-carboxymethyl- 3-indolyl-acetic acid derivative of the general formula in an inert solvent and heating the resulting solution until evolution of carbon dioxide ceases. Novel 2 - carboxymethyl - 3 - indolylacetic acid derivatives of the second general formula above are prepared (a) by treatment of a 3- indolylacetic acid derivative of the general formula with 1 equivalent of methyl diazoacetate and deesterifieation of the resulting 2-methoxycarbonylmethyl - 3 - indolylacetic acid derivative of the general formula with lithium iodide and 2,6-lutidine; (b) by treatment of an indole derivative of the general formula with 2 equivalents of methyl diazoacetate and de-esterification of the resulting methyl 2-methoxy - carbonylmethyl - indole 3 - acetate of the general formula with lithium iodide and 2,6-lutidine; or (c) by reaction of p-anisidine or N,N-dimethylphenylene diamine with a 3-keto-4-halo-adipate of the general formula wherein R<SP>1</SP> is a lower alkyl, aralkyl or dihydropyranyl-2 group and X is bromine, chlorine or iodine, treatment of the resulting indole-2,3-diacetate of the general formula with a p.chlorobenzoyl halide and de-esterification of the obtained N-acylated indole derivative of the general formula with lithium iodide and 2,6-lutidine.
GB3764267A 1966-08-25 1967-08-16 Indole Derivatives Expired GB1161637A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA968822 1966-08-25

Publications (1)

Publication Number Publication Date
GB1161637A true GB1161637A (en) 1969-08-13

Family

ID=4142644

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3764267A Expired GB1161637A (en) 1966-08-25 1967-08-16 Indole Derivatives

Country Status (4)

Country Link
CH (1) CH487149A (en)
DE (1) DE1695475A1 (en)
GB (1) GB1161637A (en)
NL (1) NL6711393A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483477A (en) * 2019-07-18 2019-11-22 江汉大学 A kind of diamine monomer and preparation method thereof containing pyridine and indole structure

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110483477A (en) * 2019-07-18 2019-11-22 江汉大学 A kind of diamine monomer and preparation method thereof containing pyridine and indole structure

Also Published As

Publication number Publication date
NL6711393A (en) 1968-02-26
CH487149A (en) 1970-03-15
DE1695475A1 (en) 1971-04-15

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees