2-Amino-5-methylbenzoic acid → 3-Methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acid

HRID 1076187Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>>[CH3:19][C:16]1[CH:15]=[C:11]([C:12]([OH:14])=[O:13])[C:10]2[NH:9][C:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=3[C:18]=2[CH:17]=1

Participants

Reactant 2

HCID 762552-Amino-5-methylbenzoic acid

HCID 117897582-Bromocyclohexanone

Product 1

HCID 117759873-Methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acidYield 55%

Procedure

Under the conditions of Example 60, 2-bromocyclohexanone is reacted with the methyl ester of 2-amino-5-methylbenzoic acid; after recrystallization from cyclohexane, the methyl ester of 3-methyl-5,6,7,8-tetrahydrocarbazole-1-carboxylic acid is obtained in a 55% yield, m.p. 111° C.

Workup

customafter recrystallization from cyclohexane

Sources & evidence

ORD record: ord-28d549f2b70c47fca2e31f3628980678
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956295

Reaction notes

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