Acetic Acid → HCID 135838170, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(6-(bromomethyl)-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.28 g, 0.72 mmole) in 0.3 M sodium methoxide (25 ml) was stirred and heated at 650° C. under a nitrogen atmosphere for 4 hours. After cooling, the mixture was acidified to pH 6 with glacial acetic acid, and then all solvent was removed under reduced pressure. The residue was triturated with water (20 ml), then filtered, washed with water and acetone, and dried to give 3-amino-6-(methoxymethyl)benzo[f]quinazolin-1(2H)-one as an off-white solid. (0.12 g, 58%) 1H NMR (DMSO-d6, 200 MHz) d 3.39 (s, 3H, OCH3); 4.85 (s, 2H, CH2); 6.54 (br s, 2H, NH2); 7.33 (s, 1H, Ar); 7.44 (dt, J=6.9, 1.4 Hz, 1H, Ar); 7.59 (dt, J=6.9, 1.4 Hz, 1H, Ar); 7.96 (dd, J=8.2, 1.0 Hz, 1H, Ar); 9.69 (d, J=8 Hz, 1H, Ar); 11.11 (br s, 1H, NH); 11.91 (br s, <1H, pyr-NH+). Anal. Calculated for C14H13N3O2.1/2HOAc.1/10H2O: C, 62.75; H, 5.34; N, 14.64. Found C, 62.74; H, 5.31; N, 14.64.

Provenance & Evidence