[C:1]1(=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>O.C1COCC1.CO>[C:1]1(=[N:15][OH:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1To a mixture of 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one (12.2 g, 70.9 mmol), hydroxylamine hydrochloride (7.85 g) and water (90 ml) were slowly added sodium acetate (14.5 g), methanol (120 ml), THF (30 ml) and water (60 ml) with stirring while heating at 75° C., and the mixture was stirred for 2 hr and 40 min. After cooling to room temperature, methanol was evaporated under reduced pressure, and the obtained precipitate was collected by filtration, and washed with water to give 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one oxime (13.5 g).
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