Sodium Hydroxide → 5-Methoxy-6-(trifluoromethyl)indoline

Participants

Reaction Steps

The indole (D2) (67.63 g, 0.315 mol) in glacial acetic acid (500 ml) was treated with sodium cyanoborohydride (40 g, 0.637 mol) portionwise at room temperature with stirring. After 3 h at room temperature the reaction mixture was diluted with water (500 ml) and basified with 40% aqueous NaOH with cooling. The mixture was then extracted with dichloromethane (3×500 ml) and the combined extracts were dried (Na2SO4) and evaporated to give the title compound (67.73 g, 99%) as an off-white solid.

Provenance & Evidence