Sodium Hydroxide → 6-Chloro-1-propyl-1H-indole-3-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14](=[O:19])C(F)(F)F)=[CH:7][N:8]2[CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[OH-:20].[Na+]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]([OH:19])=[O:20])=[CH:7][N:8]2[CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 1-(6-chloro-1-propyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone (277.1 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., partitioned between water (75 mL) and ethyl acetate (75 mL), and 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-propyl-1H-indole-3-carboxylic acid (141.4 mg, 74%) as a cream-colored solid: mp 179-180° C.; EI-HRMS m/e calcd for C12H12ClNO2 (M+) 237.0556, found 237.0558.
Workup
- temperaturewas heated
- temperatureunder reflux for 17 h
- custompartitioned between water (75 mL) and ethyl acetate (75 mL)
- extractionextracted 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-828f16293d16474eaf8e7be974d468a4
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881844B2
Reaction notes
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