Nitric Acid → 2-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-1,2,3,4-tetrahydroquinoline (D63) (383 mg, 2.6 mmol) in concentrated sulfuric acid (7.2 ml) at 0-5° C. was added concentrated nitric acid (0.26 ml) dropwise so as to maintain the temperature at 0-5° C. On completion of addition, the mixture was warmed to room temperature, stirred for 45 mins. then poured onto crushed ice and neutralised with 2M sodium hydroxide solution. The mixture was extracted with DCM which was washed with brine, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 10% EtOAc in 60-80° C. petroleum ether gave the title compound as an orange solid (297 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.40 (dd, 1H), 7.27 (d, 1H), 7.03 (d, 1H), 4.01 (br, 1H), 3.46 (m, 1H), 2.87 (m, 2H), 1.92 (m, 1H), 1.59 (m, 1H), 1.24 (d, 3H).

Provenance & Evidence