Hydrochloric Acid → HCID 15567167, compound

Participants

Reaction Conditions

Reaction Steps

50 ml of concentrated aqueous hydrochloric acid were added, while cooling (reaction temperature: max. +20° C.) to a solution of 26.6 gm (0.174 mol) of 3,5-dimethoxyaniline in 100 ml of glacial acetic acid. Over a period of 35 minutes a solution of 12 gm (0.174 mol) of sodium nitrite in 25 ml of water was added at -8° to -3° C. while cooling. After stirring for 1 hour on a cold bath, the reaction mixture was filtered, and the dark-brown filtrate was poured at 20°-25° C. into a stirred suspension of 10.2 gm (60 mmols) of copper (II)-chloride and 2 gm (20 mmols) of copper(I)-chloride in 120 ml of a 30% solution of sulfur dioxide in glacial acetic acid. The reaction temperature first rose to 40° C. and after it fell the reaction mixture was heated at 40° C. for another 90 minutes. After partial evaporation, the reaction mixture was poured into 2 liters of ice water. After three extractions with ether, the organic extracts were washed with water, sodium bicarbonate solution and again with water.

Provenance & Evidence