4-Nitroso-N,N-dimethylaniline [138-89-6-A] C8H10N2O
In a 250-ml beaker, dissolve 12.7 ml of N,N-dimethylaniline in 40 ml of concentrated hydrochloric acid and add 10 g of ice. While cooling externally with ice and stirring, add a solution of 8.3 g of sodium nitrite in 30 ml of water, keeping the temperature below 5 °C. No nitrous gases should form during the correct reaction. Leave the reaction mixture in the ice bath for another 15 minutes. Subsequently, filter off the yellow crystals of 4-Nitroso-N,N-dimethylaniline hydrochloride and wash initially with cold dilute hydrochloric acid and then with ethanol. To obtain 4-Nitroso-N,N-dimethylaniline in its free base form, carefully alkalize the hydrochloride with dilute soda solution. Extract with ether until no more green color is extracted. Concentrate the ether phase until crystallization begins. The obtained crystals have a melting point of 88 °C.
Description: 4-Nitroso-N,N-dimethylaniline forms green needles and is used as an intermediate for dyes and pharmaceuticals.
Source: Based on Org. Synth. Coll. Vol. 3, p. 663 (1955); Org. Synth. 26, 66 (1946).
Delivered by: Mephisto
Last updated: 31/10/2007
Other names: N,N-Dimethyl-p-nitrosoaniline; 4-Nitroso-N,N-dimethylbenzenamine