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

HRID 392214Notes

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-1H-indole-6-carboxylate [9.0 g, Reference Example 29(a)] 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-67e5b10e79ba4e80bbec0a5fd3a55a79
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800645B1

Reaction notes

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