Sodium Hydroxide → HCID 13324715, compound

Participants

Reaction Steps

A solution of 4.0 g (16.1 mmole) of 3-(5-methoxy-1-indolyl)benzonitrile of Example 9a in 160 ml glacial acetic acid under nitrogen at 15°-20° C. was treated with 3.14 g (49.9 mmole, 3.1 equivalents) sodium cyanoborohydride. The reaction mixture was permitted to warm to room temperature and stir overnight (about 16 hours). The resulting solution was poured over ice (200 ml), made basic using 50% NaOH (165 ml) and extracted with chloroform (350 ml total). The combined organic extracts were washed with water (400 ml), brine (400 ml), dried over Na2SO4, and concentrated to give 3.90 g (96.8%) of the crude indoline as an oil. Crystallization from hot ethyl acetate-hexane afforded 1.87 g (46.4% overall) of 3-(5-methoxy-1-indolinyl)benzonitrile, m.p. 92.5°-93.5° C.

Provenance & Evidence