Ethenamine, N,N-dimethyl-2-nitro- → 4-Ethoxycarbonyl-3-(2-nitrovinyl)indole
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)=[O:5])[CH3:2].CN([CH:18]=[CH:19][N+:20]([O-:22])=[O:21])C>C(OCC(F)(F)F)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH:18]=[CH:19][N+:20]([O-:22])=[O:21])=[CH:9][NH:10]2)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g of 4-ethoxycarbonyl indole are added to a solution of 3.1 g of dimethylamino-2-nitroethylene in 20 ml of trifluoroethyl acetate refrigerated under argon. The reaction mixture is introduced into ice water after it had been standing overnight at room temperature. The aqueous phase is repeatedly extracted with ethyl acetate. The combined ethyl acetate extracts are extracted first with sodium bicarbonate solution, then a saturated sodium chloride solution, dried and evaporated. The residue is recrystallized from ethanol. Yield: 4.5 g of 4-ethoxycarbonyl-3-(2-nitrovinyl)-indole. Yellow crystals with a 197°-199° C. melting point.