6-Methoxy-3,4-dihydro-1H-quinolin-2-one

NaNO2 (19.2 g, 0.11 mmol) was added portion wise to a solution of 6-methoxy-3, 4- dihydroquinolin-2(1H)-one (8.2 g, 0.12 mmol) in TFA (150 mL) at 0 C, then the reaction mixture was stirred at RT for 0.5 h. The mixture was poured into ice water (60 mL) and filtered. The cake was washed with ether (20 mL) and dried in vacuuo to afford the crude product which was used in the next step without further purification. (15 g, 63 %)C. 6-Methoxy-3, 4-dihydrocarbostyril. To a solution, prepared by mixing 8.2 g. 6-hydroxy-3, 4-dihydrocarbostyril with 50 ml. water containing 2 g. sodium hydroxide, was added dropwise with stirring 8.5 ml. dimethyl sulfate (sp. gr. 1.332). During the course of the addition the resulting mixture was maintained at about pH10 by periodic additions of 10% sodium hydroxide solution. The mixture was stirred for 21/2 hours at room temperature, filtered and the collected solids were washed thoroughly with water to give after recrystallization from methyl alcohol 6.3 g. 6-methoxy-3, 4-dihydrocarbostyril; m.p. 142.5-143.5C.C. 6-Methoxy-3, 4-dihydrocarbostyril To a solution, prepared by mixing 8.2 g. 6-hydroxy-3, 4-dihydrocarbostyril with 50 ml. water containing 2 g. sodium hydroxide, was added dropwise with stirring 8.5 ml. dimethyl sulfate (sp. gr. 1.332). During the course of the addition the resulting mixture was maintained at about pH 10 by periodic additions of 10% sodium hydroxide solution. The mixture was stirred for two and one-half hours at room temperature, filtered and the collected solids were washed thoroughly with water to give after recrystallization from methyl alcohol 6.3 g. 6-methoxy-3, 4-dihydrocarbostyril; m.p. 142.5-143.5 C.Compound I-2 (177 mg, 1 mmol), ferric trichloride hexahydrate (2.7 mg, 0.01 mmol) and sodium peroxodisulfate (286 mg, 1.2 mmol) were added to a reaction flask with a reflux condenser, and acetonitrile (5 mL) was added. ) And water (5 mL) and stir well at room temperature. The mixture was stirred with heating at 80 C for 2-3 hours until the reaction was completed. The reaction mixture was concentrated by heating to remove most of the acetonitrile, and then slowly cooled to room temperature, and a solid was gradually precipitated. The product was dried by filtration to obtain 154 mg of the product II-2 as an off-white solid, with a yield of 88%.

Molecular Weight:177.20
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:177.078978594
Monoisotopic Mass:177.078978594
Topological Polar Surface Area:38.3
Heavy Atom Count:13
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes