Hydrochloric Acid → 1-Methyl-1,2,3,4-tetrahydroquinolin-7-ol

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Reaction Steps

(0.093 mole) was dissolved in a mixture of methanol 105 ml., water 70 ml., and concentrated hydrochloric acid 35 ml. and was filtered into a 500 ml. conical flask. The solution was well cooled to maintain a temperature between 0° and 5° and was rapidly stirred whilst a 10% aqueous solution of sodium nitrite 67 ml. (5% excess) mixed with methanol 67 ml. was slowly dripped in over half an hour and then stirred for another hour. The precipitate was filtered, washed with cold, dilute hydrochloric acid and air-dried to give 11.7 g. (56%) of yellow-brown fine crystals of 1-methyl-1,2,3,4-tetrahydro-6-nitroso-7-hydroxyquinoline hydrochloride.

Provenance & Evidence