913613-84-0|7-Methoxy-3-methylquinolin-2(1H)-one| Ambeed

Yield	Reaction Conditions	Operation in experiment
	With triethylsilane; trifluoroacetic acid; at 20℃; for 16h;Cooling with ice;	To an ice-cooled solution of 7-methoxy-2-oxo- 1 ,2-dihydroquinoline-3-carbaldehyde (6 g, 29.55 mmol) in TFA (110 mL) was added triethyl silane (13.2 mL) drop wise and stirred at RT for 16h. Reaction mixture was poured into ice water; solid was filtered off and washed with water, dried under reduced pressure for overnight to give title compound as pale yellow solidcrude (6 g). 1H NMR (400 MHz, DMSO-d6) oe 11.59 (s, 1H), 7.67 (s, 1H), 7.48 (d, J=8.8 Hz,1H), 6.78-6.75 (m, 2H), 3.78 (s, 3H), 2.04 (s, 3H); LC-MS: mlz 190.1 (M+1).
	With triethylsilane; trifluoroacetic acid; at 20℃; for 16h;Cooling with ice;	Step-d Synthesis of 7-methoxy-3-methylquinolin-2(1H)-one To an ice-cooled solution of <strong>[101382-55-2]7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde</strong> (6 g, 29.55 mmol) in TFA (110 mL) was added triethyl silane (13.2 mL) drop wise and stirred at RT for 16 h. Reaction mixture was poured into ice water; solid was filtered off and washed with water, dried under reduced pressure for overnight to give title compound as pale yellow solid crude (6 g). 1H NMR (400 MHz, DMSO-d6) delta 11.59 (s, 1H), 7.67 (s, 1H), 7.48 (d, J=8.8 Hz, 1H), 6.78-6.75 (m, 2H), 3.78 (s, 3H), 2.04 (s, 3H); LC-MS: m/z 190.1 (M+1)+.
	With triethylsilane; trifluoroacetic acid; at 0 - 20℃;	30.7 ml of triethylsilane was added to a trifluoroacetic acid (300 ml) solution of 13 g of 7- methoxy-2-oxo-l, 2-dihydroquinoline-3-carbaldehyde while EPO <DP n="49"/>being stirred under ice-cooling and stirred at room temperature overnight. The reaction solution was poured into ice water and extracted with dichloromethane and, after washed with water, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(dichloromethane :methanol = 30:1), and 11.1 g of 7- methoxy-3-methyl-lH-quinolin-2-one was obtained in the form of a white powder. 1H-NMR ( DMSO-ds) deltappm:2.02(3H, s) , 3.77(3H, s) , 6.70-6.80 (2H, m) , 7.45(1H, d, J=8.4Hz), 7.64(1H, s) , 11.56(1H, brs).

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7-Methoxy-3-methylquinolin-2(1H)-one

CAS No.: 913613-84-0

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