Hydrazine → HCID 135988232, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-acetyl-4-hydroxybenzo[g]quinolin-2(1H)-one (1-4) (3.95 g, 15.6 mmol, 1.0 equiv), hydrazine (0.74 ml, 0.75 g, 23.4 mmol, 1.5 equiv), and catalytic conc. HCl (2 drops) in DMA (30 ml) were heated to 140° C. under nitrogen for 55 hours. The solution was cooled and the solid precipitate was filtered, washed with methanol (100 ml×3), and dried to yield 3-methyl-2,5-dihydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-5) as a tan solid. 1H NMR (500 MHz, DMSO-d6)) δ 11.14 (s, 1H), 8.61 (s, 1H), 7.97 (d, 1H, J=8.0 Hz) 7.85 (d, 1H, J=8.5 Hz), 7.70 (s, 1H), 7.50 (m, 1H), 7.41 (m, 1H), 2.59 (s, 3H). LRMS m/z/z (M+H) 250.2 found, 250.1 required.

Provenance & Evidence