2-Methyl-6-nitrobenzaldehyde → 4-Methyl-2,1-benzisoxazole

Participants

Reaction Steps

To a solution of 49.64 g (220 mmoles) stannous chloride dihydrate in 132 ml concentrated hydrochloric acid cooled to 15° was added 9.08 g (55.0 mmoles) of 6-methyl-2-nitrobenzaldehyde with rapid stirring. After 2 hours the mixture was diluted with 250 ml water and extracted with 3×150 ml ether. The extract was washed successively with dilute sodium bicarbonate solution, water, and brine, dried, and concentrated to give 6.78 g oil. The oil was flash chromatographed, eluting with chloroform to give 6.10 g (83%) (1) as an oil; nmr (deuteriochloroform): 2.5 (s, 3H), 6.7 (dd, 1H), 7.3 (m, 2H), 9.1 (s, 1H).

Provenance & Evidence