Nitric Acid → N,N-Dimethyl-2-(7-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine

Participants

Reaction Steps

A solution of compound 3 (0.87 g, 4.285 mmol) in con. H2SO4 (10 mL) was treated with fuming HNO3 (0.2 mL, 4.285 mmol, 90%) drop wise over a period of 10 min. at 0° C. and was stirred at same temperature for additional 20 min. The reaction was diluted with water (50 mL), basified to pH ˜10 using 2 N NaOH solution and product was extracted into CH2Cl2 (3×20 mL). The combined organic layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5 to obtain compound 4 (0.85 g, 80%) including some dinitro derivative, which was separated at later stage.

Provenance & Evidence