Hydrochloric Acid → HCID 86626060, compound

Participants

Reaction Steps

Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice-cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml×3), and dried to yield the title compound as a yellow solid (34.4 g, 94%). 1H NMR: 11.70 (s, 1H), 7.90 (s, 1H), 7.50 (m, 2H), 7.35 (s, 1H), 7.20 (d, 1H), 3.90 (s, 3H); m/z: 296.

Provenance & Evidence