N-Methylformamide → 7-Bromo-3-methyl-3,4-dihydroquinazolin-4-one

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Reaction Steps

A solution of 4-bromo-2-nitrobenzoic acid (1 g, 4.1 mmol) and InCl3 (0.88 g, 4 mmol) in N-methylformamide (6 mL, 100 mmol) was stirred at reflux overnight (ca. 18 h). After it was cooled to room temperature, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (0.5 g). MS (ESI): 239 (MH+).

Provenance & Evidence