Hydrochloric Acid → 1-Cyclohexylmethyl-3-methyl-1H-indole-6-carboxylic acid

HRID 380425Notes

Reaction equation

[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]C)=[O:18])[CH:15]=3)[C:10]([CH3:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>CO>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[C:10]([CH3:21])=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of methyl 1-cyclohexylmethyl-3-methyl-1 H-indole-6-carboxylate and lithium hydroxide (8.0 g) in aqueous methanol (300 ml, 1:2, v/v) was heated at 70° C. for 4 hours. The reaction mixture was cooled to room temperature, then acidified by addition of dilute hydrochloric acid and then extracted three times with ethyl acetate (150 ml). The combined extracts were dried over sodium sulphate then evaporated to give the title compound as a white solid (7.3 g). M+271.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted three times with ethyl acetate (150 ml)
dry with materialThe combined extracts were dried over sodium sulphate
customthen evaporated

Sources & evidence

ORD record: ord-c1fc3af61252420191acb87d4635dbb1
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303600B1

Reaction notes

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