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

HRID 643842Notes

Reaction equation

HRID 643842 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-77f4939b2ee84325bf90161c649c1b24
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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