Chlorobenzene → HCID 18800935, compound
Reaction equation
CN(C[C:5]1[C:9]2[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N+:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:19])=[O:18].Cl[C:27]1C=CC=CC=1>>[N+:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]2[C:9]=1[CH:5]=[C:6]([CH2:27][CH:20]([N+:17]([O-:19])=[O:18])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH:7]2)([O-:16])=[O:15]Participants
4
Procedure
A solution of 60 g of 4-nitrogramine [J. B. Hester, J. Org. Chem. 29, 1158 (1964)] and 54 g of ethyl nitroacetate in 1.2 L of chlorobenzene was heated at 100° C. for 1.5 h. After cooling the mixture was filtered, washed with cold methylene chloride and dried in vacuo to afford 58.9 g of ethyl 3-(4-nitro-2-indolyl)-2-nitropropionate as a yellow solid: mp 159-160.5° C. Another 11 g may be recovered from the filtrate by dilution with hexane, preparative liquid chromatography [silica; methylene chloride/ethyl acetate (90:10)] and recrystallization from methanol. The structure was confirmed by NMR.