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

Participants

Reaction Steps

5 The indole (D8) (67.63 g, 0.315 mol) in glacial acetic acid (500 ml) was treated with sodium cyanoborohydride (40 g, 0.637 mol) 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