Benzeneacetic acid, hydrazide → HCID 86613118, compound

Participants

Reaction Steps

5-Bromo-8-methoxy-N′-(phenylacetyl)[1,6]naphthyridine-7-carbohydrazide. To a solution of 5-bromo-8-methoxy[1,6]naphthyridine-7-carboxylic acid (284 mg, 1.00 mmol) in dichloromethane (25 mL) was added phenylacetic hydrazide (137 mg, 1.00 mmol), 1-hydroxybenzotriazole hydrate (4 mg, 0.0301 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (212 mg, 1.10 mmol). The reaction mixture was stirred at room temperature for 3 hours, during which time a large amount of white solids formed. The reaction mixture was then partitioned between water and dichloromethane (a large excess of dichloromethane was needed to solubilize product). The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0% to 10% methanol in dichloromethane) to provide 5-bromo-8-methoxy-N-(phenylacetyl)[1,6]naphthyridine-7-carbohydrazide (328 mg, 79%) as a white solid. 1H NMR (DMSO-d6) δ 10.50 (d, J=1.6 Hz, 1H), 10.44 (d, J=1.6 Hz, 1 H), 9.27 (dd, J=4.0, 1.6 Hz, 1H), 8.63 (dd, J=8.8, 1.6 Hz, 1H), 7.94 (dd, J=8.8, 4.0 Hz, 1H), 7.36-7.26 (m, 5 H), 4.16 (s, 3H), 3.57 (s, 2 H); MS m/z 415 (M+1).

Provenance & Evidence