2-Chloro-4-nitrotoluene → (E)-2-(2-chloro-4-nitrophenyl)-N,N-dimethylethenamine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].C(O[CH:17](N(C)C)[N:18]([CH3:20])[CH3:19])(C)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1/[CH:11]=[CH:17]/[N:18]([CH3:20])[CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A reaction mixture of 8.49 g (48 mmol) of 2-chloro-4-nitrotoluene and 15.03 mL (72.8 mmol) of tert-butoxybis(dimethylamino)methane in 200 mL of THF is refluxed for 8 hours. The reaction solution is evaporated down and the residue is combined with petroleum ether. The precipitate is filtered off, rinsed with petroleum ether and dried at ambient temperature under a high vacuum. The product is used in other reactions without further purification. Yield: 11 g, C10H11ClN2O2 (M=226.66); calc.: molecular ion peak (M+H)+: 227/229; found: molecular ion peak (M+H)+: 227/229; Rf value: 0.55 (silica gel, petroleum ether/ethyl acetate (3:1)).