Aniline → HCID 9836975, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (3 ml), 2-cyano-4-nitroaniline (489 mg, 3.0 mmol) was added during 40 minutes, while maintaining the temperature of the reaction mixture at 23-27° C. At the end of the addition of the aniline, extra t-butylnitrite (180 μl, 1.5 mmol) was added to the reaction mixture which then was stirred at 26° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 367 mg (65%) of allyl-2-cyano-4-nitrobenzene as an orange oil. 1H NMR (CDCl3, 400 MHz) δ 8.51, (d, 1H, J=2.4 Hz), 8.39, (dd, 1H, J=8.6, 2.4 Hz), 7.58, (dd, 1H, J=8.6, 0.5 Hz), 6.00-5.90, (m, 1H), 5.29-5.17, (m, 2H), 3.74, (d, 2H, J=6.6 Hz); 13C NMR (CDCl3, 100 MHz) δ 151.3, 146.8, 133.5, 131.4, 128.4,127.9, 119.6, 116.2, 114.4, 38.9; Anal HRMS Calcd. for C10H8N2O2 (M): 188.0585.

Provenance & Evidence