Oxalyl chloride → 5-Methoxy-2-nitrobenzoyl chloride

HRID 440556Notes

Reaction equation

HRID 440556 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].C(Cl)(=O)C([Cl:18])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8]([Cl:18])=[O:9]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 3392095-Methoxy-2-nitrobenzoic acid

Product 1

HCID 125115535-Methoxy-2-nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 5-methoxy-2-nitrobenzoic acid (15.8 g, 0.08 mol), oxalyl chloride (25 g, 0.197 mol) and N,N-dimethylformamide (2 drops) is stirred at reflux for 4 hours, cooled, stirred at room temperature under nitrogen for several days and concentrated in vacuo to give the title product as a yellow oil which is identified by 1HNMR spectral analysis.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. stirringstirred at room temperature under nitrogen for several days
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a17cb54396d4d32a732003fbfbd032a
Source dataset
uspto-grants-1996_05
Patent number
US05519133

Reaction notes

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