Sodium Hydroxide → HCID 22497233, compound

HRID 1816133Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16](=[O:21])C(F)(F)F)=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[OH-:22].[Na+]>O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([OH:21])=[O:22])=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-[6-chloro-1-(3-methyl-butyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone (284.9 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-(3-methyl-butyl)-1H-indole-3-carboxylic acid (149.3 mg, 69.5%) as a light orange solid: mp 53-55° C.; EI-HRMS m/e calcd for C14H16ClNO2 (M+) 265.0870, found 265.0860.

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-5a062aca579e4dbb9d9f3804e5aa2f95
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881844B2

Reaction notes

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