Dimethylformamide → 2-Methyl-4-nitrobenzamide

HRID 409416Notes

Reaction equation

HRID 409416 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:15](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 747904-Nitro-o-toluic acid

Product 1

HCID 201651202-Methyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methyl-4-nitrobenzoic acid suspended in CH2Cl2 under Ar was added DMF then oxalyl chloride. The reaction was stirred at room temperature 1.5 hours then the solvent was evaporated. The residue was dissolved in THF and ammonia gas was bubbled through the reaction for 15 minutes. The solvent was evaporated and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The extracts were dried (MgSO4), filtered and evaporated. Column chromatography (SiO2, 0-100% EtOAc/Hex) gave pure 2-methyl-4-nitrobenzamide (E111).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in THF
  3. customammonia gas was bubbled through the reaction for 15 minutes
  4. customThe solvent was evaporated
  5. customthe residue partitioned between EtOAc and water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialThe extracts were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6c1584b71f93400480f3ca8473cf2107
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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