Dimethylformamide → 4-Methoxy-2-nitrobenzene-1-carboximidic acid

HRID 1443424Notes

Reaction equation

HRID 1443424 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.C[N:16](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:16])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2886574-Methoxy-2-nitrobenzoic acid

Product 1

HCID 1185584-Methoxy-2-nitrobenzene-1-carboximidic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled suspension of 4-methoxy-2-nitro-benzoic acid (14.1 g, 71.5 mmol) and some drops of DMF in DCM (150 ml) was added drop wise oxalyl chloride (19.0 g, 150 mmol) and the mixture was stirred for two hours at room temperature. The solvent was evaporated and water was added. The product was filtered of and washed with water and hexane. The product was dried in vacuum. Yield: 10 g, 71%.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. filtrationThe product was filtered of and
  4. washwashed with water and hexane
  5. customThe product was dried in vacuum

Sources & evidence

ORD record
ord-70d891af40ed42aeb00271826768690c
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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