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

HRID 1292949Notes

Reaction equation

HRID 1292949 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

5

Reactant 2

HCID 86279Benzamide, 2-chloro-6-nitro-HCID 4247255tert-butyl N-(2-oxoethyl)carbamate

Product 1

HCID 91152696HCID 91152696, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between sat. NaHCO3 and EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b92ddf35f0814080b320ff548fab4f2b
Source dataset
uspto-grants-2007_07
Patent number
US07238702B2

Reaction notes

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