(Z)-1-(hydroxyiMino)-3-Methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one synthesis

Yield:253324-90-2 72%

Reaction Conditions:

with sodium ethanolate in ethanol at 50; for 5 h;Product distribution / selectivity;

Steps:

A3; A4

[Example A3] Preparation of 1-(hydroxyimino)-3-methyl-1,3,4,5-tetrahydrobenz[d]azepin-2-one 3.11 g (12.5 mmol) of ethyl hydroxyimino-[2-(2-methylaminoethyl)phenyl]acetate obtained by the method of Example A2, 4.25 g (12.5 mmol) of sodium ethoxide-20% ethanol solution, and 9.3 ml of ethanol were added into a flask, and reacted at 50°C for seven hours. The resultant mixture was cooled down to a room temperature, added with 0.72 ml of acetic acid, and concentrated. Thus generated solid was added with ethyl acetate and water, followed by stirring. The precipitation was filtered and washed to obtain 1.87 g (9.2 mmol, yield 72%) of 1-(hydroxyimino)-3-methyl-1,3,4,5-tetrahydrobenz[d]azepin-2-one as a light brown solid. ¹H-NMR (400 MHz, CDCl₃) δ 3.08 (3H, s), 3.10-3.16 (2H, m), 3.70-3.76 (2H, m), 7.20-7.29 (2H, m), 7.30-7.35 (1H, m), 7.74-7.78 (1H, m), 8.78 (1H, brs).

References:

EP1985615,2008,A1 Location in patent:Page/Page column 17-18