4-Nitrobenzoyl chloride → 6,11Dihydro-5-(4-nitrobenzoyl)-5H-dibenz[b,e]azepine

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Reaction Steps

A mixture of 2.34 g (12 mmol) of 6,11-dihydro-5H-dibenz[b,e]azepine, 2.23 g (12 mmol) of 4-nitrobenzoyl chloride, 1.94 g (15 mmol) of diisopropylethylamine and 70.5 mg of 4-(dimethylamino)pyridine in 25 ml of dichloromethane is stirred at room temperature for 2 hours, refluxed for 3 hours and allowed to stand at room temperature for 2 days. The mixture is washed with water, 1N sodium bicarbonate, water, 1N HCl, brine and dried (Na2SO4). The solvent is removed to give 4.0 g of solid. Trituration with ethyl acetate and filtering gives 2.85 g of off-white crystals, m.p. 185°-188° C. Anal. Calc'd for C21 H16N2O3 0.5 H2O: C,71.4; H,4.7; N,7.9. Found: C,71.5; H,4.5; N,7.9.

Provenance & Evidence