Sodium Hydroxide → 1-isopropyl-6-methyl-1H-indole-3-carboxylic acid
Reaction equation
FC(F)(F)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[N:7]([CH:15]([CH3:17])[CH3:16])[CH:6]=1)=[O:4].[OH-:20].[Na+]>>[CH:15]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[C:5]([C:3]([OH:4])=[O:20])=[CH:6]1)([CH3:17])[CH3:16]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-methyl-1H-indol-3-yl)-ethanone (1.50 g, 5.57 mmol) in a 20% aqueous sodium hydroxide solution (20 mL) was heated at 110° C. for 18 h. At this time, the reaction was cooled to 25° C., partitioned between water (150 mL) and ethyl acetate (150 mL), and then treated with a 1N aqueous hydrochloric acid solution (50 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (1×50 mL), water (1×50 mL), and a saturated aqueous sodium chloride solution (1×50 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-methyl-1H-indole-3-carboxylic acid (1.19 g, 98%) as a yellow solid: mp 185-186° C.; EI-HRMS m/e calcd for C13H15NO2 (M+) 217.1103, found 217.1110.
Workup
- custompartitioned between water (150 mL) and ethyl acetate (150 mL)
- additiontreated with a 1N aqueous hydrochloric acid solution (50 mL)
- washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (1×50 mL), water (1×50 mL)
- dry with materialThe organic layer was then dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bbfe11bf86cc404083a9e6923167dc90
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881844B2
Reaction notes
Loading…