Hydrochloric Acid → HCID 54732146, compound

Participants

Reaction Steps

33.8 g. (0.21 mol) of 4-hydroxy-coumarin, 140 ml. of acetone, 40 g. of sodium acetate and 6.6 g. of cuprous chloride are placed in a one-liter reactor. The mixture is brought to a temperature lower than 5° C. There are then added dropwise a solution of the diazonium chloride of 3,4-dichloro-aniline, prepared from 32.4 g. (0.2 mol) of 3,4-dichloro-aniline, 80 ml. of concentrated hydrochloric acid, 120 ml. of water and 20 g. (0.33 mol) of sodium nitrite. A slight liberation of nitrogen is found. The substance is left for one hour between -8° C. and -5° C. and it is then brought for one hour to 50° C. The acetone is then evaporated under vacuum. A pH value of 1 is adjusted. The chestnut-coloured precipitate is taken up under heat in 2 liters of a 5% solution of sodium bicarbonate, followed by filtration and then the filtrate is acidified with HCl. The product obtained is recovered, washed with water, dried and recrystallised from a mixture of ethanol and water (70-30). A chestnut-coloured product is obtained. Weight 9.8 g.; yield 16% (theoretical yield 51.4 g.); M.P. 262° C.

Provenance & Evidence