Ethyl chloroformate → HCID 57559687, compound

Participants

Reaction Steps

To a solution of 3-amino-2-naphthoic acid (3.74 g, 20.0 mmol, 1 equiv.) in pyridine (40 ml) at −10° C. under nitrogen was added ethyl chloroformate (7.6 ml, 8.63 g, 79.5 mmol, 4.0 equiv) dropwise over an hour. The reaction was stirred from −10° C. to room temperature over 20 hours. The solvent was evaporated under reduced pressure, water (100 ml) was added to the solid residue, and the mixture was stirred at room temperature for 1 hour. The precipitate was filtered, washed with water and dried to yield 2-ethoxy-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-2) as a tan solid. LRMS m/z (M+H) 242.2 found, 242.1 required.

Provenance & Evidence