8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while being cooled with the ice bath. c) 8-acetyl-6-benzyloxy-4H-benzo[1, 4]oxazin-3-one: 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while cooling with the ice bath. Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature. The hot reaction mixture is filtered, then evaporated down to about 400 mL and combined with ice water. The precipitate formed is suction filtered, dried and purified chromatography on a short silica gel column (dichloromethane:methanol=99:1). The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]1000 ml three-neck bottle in, under the condition of ice, to compounds 1 - 7 (159 mmol), potassium carbonate (65.8 g, 477 mmol) of acetonitrile (700 ml) solution adds by drops the chlorine acetyl chloride (27 g, 238 mmol), room temperature reaction 4 h, continue to heating to reflux the reaction 16 h. The condiments filtering, the filtrate is concentrated to 200 ml, is added to the 1 L ice water, ice bath conditions for the continuation of stirring 1 h, filtered, washed with water, drying. The resulting solid silica gel column purification (dichloromethane: methanol=99:1), after concentration isopropyl alcohol/methyl cyclohexane recrystallized, filtering to obtain light brown color solid product 17.53 g.21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while being cooled with the ice bath. c) 8-acetyl-6-benzyloxy-4H-benzo[1, 4]oxazin-3-one: 21.0 mL (258 mmol) chloroacetyl chloride are added dropwise to 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone and 70.0 g (506 mmol) potassium carbonate while cooling with the ice bath. Then the mixture is stirred overnight at ambient temperature and then for 6 hours at reflux temperature. The hot reaction mixture is filtered, then evaporated down to about 400 mL and combined with ice water. The precipitate formed is suction filtered, dried and purified chromatography on a short silica gel column (dichloromethane:methanol=99:1). The fractions containing the product are evaporated down, suspended in isopropanol/diisopropylether, suction filtered and washed with diisopropylether. Yield: 34.6 g (50percent); mass spectroscopy [M+H]1000 ml three-neck bottle in, under the condition of ice, to compounds 1 - 7 (159 mmol), potassium carbonate (65.8 g, 477 mmol) of acetonitrile (700 ml) solution adds by drops the chlorine acetyl chloride (27 g, 238 mmol), room temperature reaction 4 h, continue to heating to reflux the reaction 16 h. The condiments filtering, the filtrate is concentrated to 200 ml, is added to the 1 L ice water, ice bath conditions for the continuation of stirring 1 h, filtered, washed with water, drying. The resulting solid silica gel column purification (dichloromethane: methanol=99:1), after concentration isopropyl alcohol/methyl cyclohexane recrystallized, filtering to obtain light brown color solid product 17.53 g.

Molecular Weight:297.30
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:297.10010796
Monoisotopic Mass:297.10010796
Topological Polar Surface Area:64.6
Heavy Atom Count:22
Complexity:419
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes