N-Methylanthranilic acid → 9-Methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acid

HRID 1076188

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:9][NH:10][C:11]1[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:13]([OH:15])=[O:14]>>[CH3:9][N:10]1[C:11]2[C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=[CH:18][C:19]=2[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2

Participants

Reactant 2

HCID 67069N-Methylanthranilic acid

HCID 117897582-Bromocyclohexanone

Product 1

HCID 213999599-Methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acidYield 15%

Procedure

Under the conditions of Example 59, 2-bromocyclohexanone is reacted with the methyl ester of N-methylanthranilic acid. After recrystallization from methanol, the methyl ester of 9-methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acid is obtained in a 15% yield, m.p. 56° C.

Workup

customAfter recrystallization from methanol

Sources & evidence

ORD record: ord-91a61c60fe79499f817ca274f3c7a212
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956295

Linked notes

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