Sodium Hydroxide → 6-chloro-1-isobutyl-1H-indole-3-carboxylic acid

HRID 1816129Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:15](=[O:20])C(F)(F)F)=[CH:7][N:8]2[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.[OH-:21].[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:15]([OH:20])=[O:21])=[CH:7][N:8]2[CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-(6-chloro-1-isobutyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (282.7 mg, 0.81 mmol) in a 20% aqueous sodium hydroxide solution (2.7 mL) was heated under reflux for 17 h. At this time, the reaction was cooled to 25° C. and was diluted with water (75 mL). This mixture was extracted with diethyl ether (1×50 mL). The aqueous layer was acidified to pH=1 with concentrated hydrochloric acid and then extracted with ethyl acetate (1×75 mL). The combined organic layers were washed with water (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 6-chloro-1-isobutyl-1H-indole-3-carboxylic acid (161.4 mg, 79%) as a cream-colored solid: mp 205-206° C.; EI-HRMS m/e calcd for C13H14ClNO2 (M+) 251.0713, found 251.0713.

Workup

temperaturewas heated
temperatureunder reflux for 17 h
extractionThis mixture was extracted with diethyl ether (1×50 mL)
extractionextracted with ethyl acetate (1×75 mL)
washThe combined organic layers were washed with water (1×50 mL)
dry with materiala saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c8801a0aad3464fbc6101a252539b5b
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881844B2

Reaction notes

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