Acetic Acid → Methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate

Participants

Reaction Steps

To a stirred solution of methyl 5-bromo-2-aminobenzoate (10.0 g) and methyl 3-amino-4-methylbenzoate (7.90 g) in toluene (100 ml) at 50° C. were added triethylorthoformate (8.12 ml) and glacial acetic acid (2.50 ml). The mixture was heated to reflux for 16 hours. The alcohol by-products were distilled using Dean-stark conditions and the reaction cooled room temperature. The resultant solid was collected by filtration, washed with toluene (2×20 ml) and dried in vacuo at 40° C. to give the methyl 3-(6-bromo-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate as a white solid (13.1 g); NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 3.85 (s, 3H), 7.60 (d, 1H), 7.71 (d, 1H), 8.01 (m, 3H), 8.26 (s, 1H), 8.34 (s, 1H); Mass Spectrum: M+H+ 373.

Provenance & Evidence