2-Ethylaniline → 2-Methylpentane

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloropyrimidine (596 mg, 4 mmol), 2-ethylaniline (494 ml, 4 mmol) and N,N-diisopropylethylamine (695 ml, 4 mmol) were dissolved in n-butanol (20 ml) with stirring. The reaction mixture was heated to 100° C. for 18 hours, allowed to cool to ambient temperature and evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with EtOAc (0–20%): isohexane to give the title product as a colourless solid on evaporation (215 mg, 23%). NMR (CDCl3, 300 MHz): 1.20 (t, 3H), 2.61 (q, 2H), 6.26 (d, 1H), 6.80 (br, 1H) 7.31 (m, 4H), 8.04 (d, 1H); m/z: (ES−) 234.2 (MH+).

Provenance & Evidence