Acetic Acid → 3-Amino-9-bromobenzo[f]quinazolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.15 g, 0.4 mmole) in 0.75 N NaOH (7 ml) was stirred and heated to 75° C. under a nitrogen atmosphere for 10.5 hours. The solution was cooled and made slightly acidic with acetic acid to cause precipitation of the product. The precipitate was collected, washed successively with water, methanol and ether, and dried to give 3-amino-9-bromobenzo[f]quinazolin 1(2H)-one as an off-white solid. (0.115 g, 99%) 1H NMR (DMSO-d6, 200 MHz) δ: 6.64 (br s, 2H, NH2); 7.31 (d, J=8.8 Hz, 1H, Ar); 7.57 (dd, J=8.5, 1.9 Hz, 1H, Ar); 7.83 (d, J=8.6 Hz, 1H, Ar); 8.02 (d, J=9.0 Hz, 1H, Ar); 9.83 (s, 1H, Ar); 11.28 (br 5, 1H, NH).

Provenance & Evidence