Phenol → Benzo[g]quinazoline-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-2-naphthoic acid (8-1,1.2 g, 6.6 mmol, 1 equiv), urea (2.0 g, 33 mmol, 5.0 equiv) and phenol (7.0 g, 74 mmol, 11 equiv) was heated at 160° C. for 0.5 h an 185° C. for an additional 1.5 h. The reaction was cooled and triturated with methanol (50 mL). The solid precipitate was filtered, washed with methanol, and dried to yield benzo[g]quinazoline-2,4(1H,3H)-dione (1-2) as an orange solid. LRMS m/z (M+H) 213.1 found, 213.1 required.

Provenance & Evidence