Hydrochloric Acid → HCID 578421, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-ethylaniline (90g.) in water (280ml.) was added concentrated hydrochloric acid (38% w/w, 280ml.), and the mixture was warmed on a steam bath. The suspension obtained was stirred and cooled to 0°C., and a solution of sodium nitrite (52.1g.) in water (180ml.) was added during 45 minutes, the temperature being maintained at -10° to -5°C. by cooling. The dark solution was stirred at 0° C. for a further 30 minutes, and then filtered through celite. The filtered diazonium salt solution (stored at 0°C.) was added in portions to a stirred fresh mixture of sodium dithionite (500g.) in ice-cold water 1 l.) keeping the temperature at 5°-10°C. After the addition of each batch of the diazonium salt solution, further dithionite (total 500g.) was added in portions. After the addition was complete (45 minutes), the mixture was stirred at room temperature overnight. The mixture was separated by filtration and the filtered solid was suspended in water (1 l.), basified with sodium hydroxide solution, and the mixture extracted with ethyl acetate (3 × 250ml.). The combined extracts were washed with a minimum of water, dried (MgSO4), and evaporated to give 4-ethylphenylhydrazine as a low melting solid.

Provenance & Evidence