Ammonium Hydroxide → 8-methoxy-5,6-dihydro-3H-benzo[f]cinnolin-2-one

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Reaction Steps

In a 50 mL round bottom flask, 6-methoxy-3,4-dihydro-1H-naphthalen-2-one (1.0 g, 5.68 mmol), and glyoxylic acid monohydrate (523 mg, 5.68 mmol), in acetic acid (10 mL) was heated to reflux 3 h. The reaction was cooled and diluted with water (20 mL). The mixture was basified to pH 8 with NH4OH and then hydrazine monohydrate (0.55 mL, 11.4 mmol) was added. The reaction was heated to reflux 2 h. The reaction was cooled and re-basified with NaHCO3, then extracted with methylene chloride three times. The organics were dried over MgSO4, and the solvents were removed under vacuum to produce 1.1 g (85%). mp dec. 270° C. MS m/z=229 (M+H).

Provenance & Evidence