Hydrochloric Acid → 3-butyl-1H-indole-5-carboxylic acid

HRID 349005

Reaction equation

[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]CC)=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of Ethyl 3-butyl-1H-indole-5-carboxylate, EXAMPLE SP-225, step2, (0.4 g) in methanol (15 mL) was added 1N NaOH (5 mL). The mixture was stirred at 50° C. for 18 h, cooled to room temperature and poured into 1N HCl (50 mL). The mixture was extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give 0.145 g of the title compound: MS (ESI+) for C13H15N1O2 m/z 216.12 (M+H)+.

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted with ethyl acetate
extractionThe ethyl acetate extract
dry with materialwas dried over anhydrous sodium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-e27f1dfe01cf4d46a5a33961c1a5c7e5
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176242B2

Linked notes

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