Dimethylformamide → 2-Fluoro-4-nitrobenzamide

HRID 1020136Notes

Reaction equation

HRID 1020136 reaction equation
[F: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>[F: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 3026792-Fluoro-4-nitrobenzoic acid

Product 1

HCID 217840942-Fluoro-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-fluoro-4-nitrobenzoic acid suspended in CH2Cl2 under Ar was added DMF then oxalyl chloride. The reaction was stirred at room temperature 1.5 h then the solvent was evaporated. The residue was dissolved in THF and ammonia gas was bubbled through the reaction for 15 min. 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-fluoro-4-nitrobenzamide (E335).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in THF
  3. customammonia gas was bubbled through the reaction for 15 min
  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-63569cfd228e437dbf95fc615ed957d4
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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