Hydrochloric Acid → HCID 10848635, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-3,4dichloro-6-nitroaniline (48.3 g, 168.9 mmol), iron powder (30.0 g, 537.2 mmol) and ethanol (1 L) were combined and the resulting suspension was cooled to 0° C. Concentrated hydrochloric acid (37%, 193.0 mL, 2.36 mol) was then added dropwise over 15 min by means of an addition funnel. The resulting mixture was heated to reflux for 1 h, after which time it was allowed to cool to room temperature. The mixture was diluted with water (1.5 L) and the pH was adjusted to approximately 8 by the addition of sodium carbonate. The product was extracted with ethyl acetate (1 L), dried over magnesium sulfate, filtered and the solvents were removed under reduced pressure using a rotary evaporator. The product was crystallized from a methanol/water mixture to afford 34.21 g (79%) of a brown solid; m.p. 128-129° C. Anal. Calcd for C6H5BrCl2N2: C, 28.16; H, 1.97; N, 10.95. Found: C, 28.29; H, 1.96; N, 10.79.

Provenance & Evidence