Hydrochloric Acid → HCID 69893747, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (50 ml, 32%, 0.5 mole) was charged to a 250 ml flask under a nitrogen atmosphere and cooled down to −2 to 0° C. 2-Bromoaniline (10 g, 0.058 moles) was added and the reaction mixture was re-cooled to −2 to 0° C. Sodium nitrite (4.8 g, 0.070 moles) dissolved in water (10 ml) was added dropwise to the acidic mixture through an addition funnel over a period of 35 minutes at −2 to 0° C. The resulting mixture (yellow suspension) was stirred for 1 hour at −2 to 0° C. L-Ascorbic acid (10.3 g, 0.058 moles) was then added portionwise as a solid over a period of 25 minutes at −2 to 0° C. The reaction was allowed to come to room temperature (18-20° C.), then heated to 40° C. and stirred for 3 hours at this temperature. The resulting slurry (red suspension) was cooled to room temperature (18-20° C.) and water (30 ml) was added. The mixture was stirred for 16 hours at 20-25° C., cooled and stirred at 0-2° C. for 1 hour, then filtered and the solid was washed with water to afford 40 g of wet 2-bromophenylhydrazido oxalic acid.

Provenance & Evidence