Reaction #2122473

Reaction equation

4-dimethylaminobenzaldehyde

nitrobenzene

methylamine

→

red crystals

Yield 41.1%

1-(p-Dimethylaminophenyl)-2-nitroethylene

Yield 41.1%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe dark red solid obtained
2. 2
   Filtrationafter filtration
3. 3
   Otherwas recrystallized from nitromethane
4. 4
   Washrinsed with cold methanol

Procedure

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).

Source