Ammonia → HCID 46835211, compound

Participants

Reaction Steps

To a 1 L round bottom flask charged with 6-bromo-4-hydroxy-7-methoxycinnoline-3-carboxylic acid (Method 18) (14 g, 46.8 mmol) was added SOCl2 (342 ml) and DMF (1 ml). The resulting mixture was heated to reflux for 4 hours before being cooled to rt. The reaction mixture was conc. in vacuo to yield a residue which was suspended in acetone (˜400 ml). The suspension was cooled to 0° C. in an ice bath and conc. aqueous ammonia (50 ml, 1284 mmol) was added drop wise via an addition funnel and the resulting mixture was allowed to stir at 0° C. for an additional 15 minutes. A precipitate formed which was collected via vacuum filtration. The filter cake was washed with water (3×100 mL), acetone (3×50 mL), collected, and dried in vacuo to yield the title compound as an off white solid (14.00 g, 94%) which was used without further purification. 1H NMR: 8.55 (s, 1H), 8.40 (s, 1H), 8.05 (m, 2H), 4.10 (s, 3H); m/z: 317.

Provenance & Evidence