Hydrochloric Acid → 1,2,3,4-Tetrahydro-1-nitrosoquinoline

Participants

Reaction Steps

266.4 g of 1,2,3,4-tetrahydroquinoline were added to a mixture of 330 ml of 12 N hydrochloric acid and 800 g of ice. A solution of 165 g of sodium nitrite in 500 ml of water was added slowly to the mixture over the course of 2 hours while the temperature was kept below 5° C. The reaction mixture was then allowed to warm to room temperature in the course of hour and was extracted twice with 500 ml portions of toluene. The organic phase was separated, washed four times with 300 ml portions of water, dried and evaporated. As a residue, 269 g of crude 1,2,3,4-tetrahydro-1-nitrosoquinoline were obtained as a brownish oil.

Provenance & Evidence