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

HRID 2054501Notes

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-88be75adfce14a1db390f3868cb40634
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329675B2

Reaction notes

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