Hydrochloric Acid → 2-Nitroso-1-naphthol

Participants

Reaction Conditions

Reaction Steps

48 g of 1-nitroso-2-naphthol are suspended in a mixture of 300 ml of water and 60 ml of 5n NaOH, then another 240 ml of 5n NaOh are added. While stirring well hot water vapor is passed through the solution until the temperature reaches 35° C. Subsequently 120 g of freshly prepared sodium dithionite is added with the temperature rapidly rising to 60° C. The solution assumes an amber-colored tint. After 15 minutes, the solution is rapidly cooled to under 20° C. by adding 200 g of ice and 100 ml of concentrated hydrochloric acid. The white, flaky precipitation is filtered by vacuum and suspended in a mixture of 500 ml of water and 50 ml concentrated hydrochloric acid. Overheated water vapor is passed into this mixture with such a volume flow that the temperature reaches 90° C. within 10 min. At this temperature is stirred another hour while reducing the vapor flow. The still hot solution is filtered with the aubergine-colored precipitation remaining. Upon cooling the filtrate, a light, flaky precipitation falls out which is sucked away, scavenged with diluted hydrochloric acid and then with ether and dried. Yielded were 45 g of 1-amino-2-naphthol-hydrochloride. The amino-hydroxy aromatic compounds were employed in all the transformations into this acidic form, because the free bases with the exception of 5-amino-6-quinoline proved to be very unstable.

Provenance & Evidence