N-Methylformanilide → HCID 23354002, compound

Participants

Reaction Steps

A mixture of 1.9 g of N-methylformanilide in 1.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 2.0 g of 2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin-3(2H)-one was added thereto. After stirring at room temperature for 10 hours, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in methanol and 1.0 g of sodium borohydride was added thereto under ice-cooling. After stirring for an hour, the mixture was poured into diluted hydrochloric acid and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The solid was recrystallized from a mixed solvent of isopropyl alcohol and isopropyl ether to give 0.2 g of 8-hydroxymethyl-2-(4-methylphenyl)-5,6-dihydrothieno-[2,3-h]cinnolin3(2H)-one as a brown powder, melting at 166°-169° C.

Provenance & Evidence