Hydrochloric Acid → HCID 20212863, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-(4-aminophenyl)acetamide (19.5 g) in concentrated hydrochloric acid (43 ml) was added an ice cold solution of sodium nitrite (9.43 g) in water (25 ml) at such a rate that the temperature of the mixture remained between -5° and +5° C. When the addition was complete the solution was stirred at 0° C. for 15 min. This was then added to a stirred solution of stannous chloride (146.3 g) in concentrated hydrochloric acid (86 ml) at -10° C. The mixture was stirred for 30 min., poured into ice cold ethanol (750 ml) and the suspension was stirred for a further 30 min. Collection of the solid by filtration and washing with ethanol followed by ether gave the title compound as a white powder (20.6 g). This material was 62% pure but was contaminated with sodium chloride. It was used in the next stage without further purification.

Provenance & Evidence