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

Temperature

80 °C

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).

1. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
2. additionwas added water (30 mL)
3. customThe contents were triturated
4. filtrationfiltered
5. washThe solid material was washed with water (2×20 mL)
6. customdried overnight

ORD record

ord-17bec9994da8474b9e94aecc696aebd1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2