Water → HCID 3089143, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-nitrophenol (46.2 g, 0.3 mol) was dissolved in diglyme (1250 mL) and added to a 3-necked, 3-liter flask equipped with a condenser, a mechanical stirrer, and a hearer. 4-Nitrobenzoyl chloride (57 g, 0.3 mol) was dissolved in diglyme (250 mL) and added to the flask. The mixture was heated, with stirring, to 120° C. for 1 hour, whereupon polyphosphoric acid (90 g) was added. Heating was continued at 150° C. to 160° C. for an additional 1 hour. The reaction mixture was cooled to 110° C. to 120° C. and deionized water (500 mL) was added over a period of 15 to 30 minutes while the mixture was maintained at 100° C. The reaction mixture was cooled, and the precipitated product was filtered and washed with methanol (300 mL), then dried. The melting point was found to be 253° C. to 255° C. The overall yield was 95 percent with an assay of 100 percent by liquid chromatography.

Provenance & Evidence