Nitric Acid → 7-Nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of 1,2,3,4-tetrahydoquinoline (6.5 g, 0.049 mol) in conc. sulfuric acid (118 mL) at 0° C. was added a solution of con. nitric acid (4.9 mL) in conc. Sulfuric acid (12 mL) drop-wise over 3 hours so as to maintain the temperature <5° C. The reaction mixture was then poured onto crushed ice and neutralized with solid potassium carbonate. The mixture was extracted with EtOAc (2×500 mL), the combined organic extracts were washed with water, dried and concentrated to give the crude product which was purified by column chromatography on silica-gel using EtOAc/hexane as eluent to obtain the title compound as an orange solid.

Provenance & Evidence