Acetyl chloride → 7-Bromo-2-methylquinazolin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1 g (4.63 mmol) 4-bromoanthranilic acid (J. Org. Chem. 1997, 62, 1240–1256), 50 mg (0.417 mmol) of 4-(dimethylamino)pyridine and 2.58 ml (18.5 mml) of triethylamine in dry DMF (5 ml) was added dropwise 0.79 ml (11.1 mmol) of acetylchloride at 3° C. for 20 min. in an ice-water bath under argon. The reaction mixture was heated at 90° C. for 3 h. and 1.32 g (13.89 mmol) of ammonium carbonate were added portionwise over 10 min., and the mixture was stirred at the same temperature for 1 h. After cooling, the mixture was poured into water and the precipitate filtered, washed with water and dried in vacuo to give 1.1 g (99.4%) of 7-bromo-2-methyl-3H-quinazolin-4-one as a light-brown solid. Mp. >191° C. (dec.). EI mass spectrum, m/e: 240 (M calculated for C9H7BrN2O: 240).

Provenance & Evidence