Hydroxyamine hydrochloride → HCID 59925101, compound

Participants

Reaction Conditions

Reaction Steps

7-Methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (used as a crude from example 1, step1, 128.8 g, 0.63 mol) and hydroxylamine hydrochloride (350 g, 5.04 mol) in pyridine (360 ml) were heated up to 80° C. The reaction mixture was stirred for 15 h at 80-90° C. Pyridine was removed under reduced pressure. The residue was partitioned between ethylacetate (2.5 l) and water (1 l). Water layer was separated and washed with ethyl acetate (1 l). Ethyl acetate solution was washed with 10% aq. KHSO4 (1 l), dried over Na2SO4. Ethyl acetate was removed under reduced pressure and the residue was crystallized from acetone to give 101.2 g of target compound. Mother liquid was concentrated to dryness and crystallized from acetone to give second crop (11.4 g). 112.6 g (82%) of the desired product was obtained. 1H NMR (CDCl3), d 9.15 (s, 1H), 7.06 (d, 1H, J=7.4 Hz) 6.92 (1H, d, J=2.4 Hz), 6.75 (dd, 1H, J=7.4 and 2.4 Hz), 3.82 (s, 3H), 2.78-2.95 (m, 4H), 1.5 (s, 6H).

Provenance & Evidence