Benzamide, 2-chloro-6-nitro- → HCID 91152696, compound

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:3]=1[C:4]([NH2:6])=[O:5].O=[CH:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:5])[NH:6][CH:15]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH:11]2

Participants

Procedure

A mixtre of 2-chloro-6-nitrobenzamide (0.3 g), iron powder (0.5 g) and t-butyl (N-2-oxoethyl)carbamate (1.0 g) in glacial acetic acid (5 mL) was heated at 50-55° C. for 2 h. The mixture was concentrated and the residue was partitioned between sat. NaHCO3 and EtOAc. The organic layer was dried (MgSO4), concentrated, and the residue was subjected to flash chromatography (silica gel/heptane-EtOAc 100:0 to 20:80 gradient) to afford the title compound as an off-white solid (0.1 g).