Urea → HCID 178487123, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-Methoxy-3,4-dihydro-2H-naphthalen-1-one (90 g, 0.511 M), urea (30.7 g, 0.511 M), triethylorthoformate (159 g, 1.07 M), ethanol (300 ml) and methane sulfonic acid (300 drops) was heated in the microwave at 90° C. for 1 hr. then cooled to room temperature. The solvent was removed under reduced pressure and the residue dried under vaccuo. The solid residue was then suspended in ethanol (250 ml) cooled to 0° C. and the precipitate was isolated via filtration and washed with ethanol (2×50 ml) and dried in vaccuo to give 8-Methoxy-5,6-dihydro-benzo[h]quinazolin-2-ol (43.95 g, 38% yield as a 1:1 urea complex) ES-MS MH+ 229.3 1H NMR (300 MHz, ppm, DMSO-d6): 11.45 (br S, 1H), 8.08 (d, 1H), 7.76 (br S, 1H), 6.95 (d, 1H), 6.91 (s, 1H), 5.4 (br S, 6H), 3.83 (s, 3H), 2.85 (m, 2H), 2.66 (m, 2H).

Provenance & Evidence