Methanol → HCID 57559684, compound

Participants

Reaction Conditions

Reaction Steps

To a dispersion of sodium hydride (95%) (0.90 g, 37.5 mmol, 2.6 equiv) in benzene (100 ml) at room temperature under nitrogen was added dropwise methanol (3.0 ml, 2.37 g, 74.1 mmol, 5.2 equiv). After stirring for 5 minutes, methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-2-naphthyl}-3-hydroxyprop-2-enoate (1-3) (5.06 g, 14.2 mmol, 1.0 equiv) was added and the reaction was heated to 72° C. for 20 hours. The solvent was evaporated under reduced pressure and the solid residue was stirred with water (50 ml) for 30 minutes followed by 1 N HCl (100 ml) for an additional 30 minutes. The solid was filtered, washed with water (100 ml) and hexanes (100 ml) and dried to yield 3-acetyl-4-hydroxybenzo[g]quinolin-2(1H)-one (1-4) as a yellow solid. LRMS m/z (M+H) 254.2 found, 254.1 required.

Provenance & Evidence