Hydroxyamine hydrochloride → 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime

Participants

Reaction Conditions

Reaction Steps

To 6-vinyl-3,4-dihydronaphthalen-1(2H)-one (Intermediate I-1B, 1.6 g, 9.29 mmol) in methanol (10 mL) was sequentially added hydroxylamine hydrochloride (0.775 g, 11.15 mmol) and sodium acetate (0.915 g, 11.15 mmol). The reaction mixture was heated at 80° C. (oil bath temp.) for 1.5 h. The reaction mixture was concentrated under reduced pressure and to the residue was added water (30 mL). The contents were triturated and filtered. The solid material was washed with water (2×20 mL) and dried overnight to yield 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (1.2 g, 6.41 mmol, 69.0% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.81-1.94 (m, 2H) 2.71-2.87 (m, 4H) 5.23-5.32 (m, 1H) 5.78 (dd, J=17.61, 0.88 Hz, 1H) 6.69 (dd, J=17.61, 10.78 Hz, 1H) 7.18 (s, 1H) 7.28 (s, 1H) 7.85 (d, J=8.14 Hz, 1H) 8.23 (br. s., 1H).

Provenance & Evidence