Benzyl Alcohol → 7-(Benzyloxy)-3,4-dihydroquinazolin-4-one

Participants

Reaction Conditions

Reaction Steps

Sodium (368 mg, 16 mmol) was added to benzyl alcohol (10 ml, 96 mmol) and the mixture was heated at 148° C. for 30 minutes, 7-fluoro-3,4-dihydroquinazolin-4-one (656 mg, 4 mmol), (J. Chem. Soc. section B 1967, 449), was added and the mixture maintained at 148° C. for 24 hours. The reaction mixture was allowed to cool, the solution was poured on to water (170 ml) and the aqueous mixture adjusted to pH3 with concentrated hydrochloric acid. The precipitate was collected by filtration, washed with water, then ether and dried under vacuum to give 7-benzyloxy-3,4-dihydroquinazolin-4-one (890 mg, 89%) as a white solid. m.p. 267-269° C. 1H NMR Spectrum: (DMSOd6; CF3COOD) 5.32(s, 2H); 7.25(d, 1H); 7.32-7.52(m, 6H); 8.12(d, 1H); 8.99(s, 1H) MS-ESI: 252 [MH]+

Provenance & Evidence