Methylamine → N,N-dimethyl-4-(2-nitroethenyl)aniline

反応式

[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[N+:12]([C:15]1C=CC=CC=1)([O-:14])=[O:13].CN>CO>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:15][N+:12]([O-:14])=[O:13])=[CH:5][CH:4]=1

参加物

実験手順

A mixture of 4-dimethylaminobenzaldehyde (1.5 g, 10 mmol) in 3 mL methanol, 0.61 g (10 mmol) nitrobenzene and 0.15 mL of 22% methylamine aqueous solution was stirred for 3 days. The dark red solid obtained after filtration was recrystallized from nitromethane and rinsed with cold methanol to yield 0.79 g (41.1%) of red crystals, mp 180.6-180.9° C. (ref mp 181° C. (see Richter-Egger, D. L. et al. J. Chem. Educ. 2001, 78, 1375-1378)). 1H NMR 3.08 (s, 6H, Ar—N(CH3)2); 6.68 (2H, d, JHH 8.7 Hz, Ar—H); 7.43 (2H, d, JHH 9.0 Hz, Ar—H); 7.50 (1H, d, JHH 13.2 Hz, Ar—CH); 7.97 (1H, d, JHH 13.5 Hz, CH—NO2).