Aniline → HCID 7923026, compound

Participants

Reaction Steps

2-Chloro-5-nitrobenzonitrile (Aldrich) (3.64 grams (hereinafter “g”), 20 millimoles (hereinafter “mmol”), aniline (2 milliliter (hereinafter “mL”), 22 mmol), N-methylpyrollidine (10 mL) and diisopropylethylamine (4 mL) were combined and heated to 120° under Ar for 18 hours (hereinafter “h”), cooled, poured into EtOAc (150 mL), washed with H2O (3×50 mL) and saturated aqueous (hereinafter “satd. aq.) NaCl (50 mL), dried (Na2SO4), concentrated, and the residue was triturated with hexane, filtered and the solid was washed with hexane and dried in vacuo to afford 4.23 g (88%) of the title compound as a light green solid. 1H NMR (400) MHz, δ: 8.45 (finely split doublet, 1), 8.19 (dd, 1), 7.48 (m,3), 7.28 (d,2), 7.06 (d, 1), 6.96 (br s,1).

Provenance & Evidence