Methanol → HCID 67216073, compound

Participants

Reaction Steps

5.2 ml (0.037 mol) of triethylamine and then, under nitrogen atmosphere at 0° C., 10 g (0.035 mol) of 4-oxo-2-phenyl-4H-3,1-benzoxazine-6-carbonyl chloride are added to 1.97 g (0.017 mol) of imidazo[1,5-a]pyridine [described in J. Chem. Soc., (1955), 2834-2836] in 100 ml of acetonitrile. After stirring at ambient temperature for 22 hours, the reaction medium is filtered. The residue obtained is washed with ethyl acetate, with water and with acetone and then dried. 0.32 g (2.65 mmol) of N,N-dimethylpyridine-4-amine is added to 9.75 g (0.026 mol) of the yellow solid obtained above in 50 ml of methanol and 50 ml of N,N-dimethylformamide. After heating at reflux for 22 hours, the reaction medium is filtered. The residue is washed with water and then dried. The product is purified by column chromatography on silica gel, elution being carried out with a mixture of dichloromethane and methanol (99.9/0.1). 3.67 g of a yellow solid are obtained. Melting point: 218° C.; 1H NMR (CDCl3): 4.05 (3H, s), 7.08-7.09 (1H, m), 7.27-7.29 (1H, m), 7.57-7.60 (3H, m), 7.76-7.81 (2H, m), 8.12 (2H, d), 8.78 (1H, d), 9.15 (1H, d), 9.28 (1H, s), 9.88 (1H, d)

Provenance & Evidence