Oxalyl chloride → Methyl 2-(chlorocarbonyl)-6-nitrobenzoate

HRID 2251859Notes

Reaction equation

HRID 2251859 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9](=[O:22])[C:10]1C(=[CH:15][CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])C(O)=O>C(Cl)Cl.CN(C=O)C>[CH3:7][O:8][C:9](=[O:22])[C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:1]=1[C:2]([Cl:4])=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2430022-(Methoxycarbonyl)-3-nitrobenzoic acid

Product 1

HCID 12651086Methyl 2-(chlorocarbonyl)-6-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (5.4 mL, 62.4 mmol) was added to a suspension of 3-nitro-phthalic acid 2-methyl ester (11.7 g, 52.0 mmol, Step A) in 150 mL of anhydrous CH2Cl2 at RT. A few drops of DMF were added, then the mixture was heated to reflux for 2 h, and cooled to RT. The mixture was washed with NaHCO3 (aq), brine, dried over MgSO4, filtered, and condensed to give the titled compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. washThe mixture was washed with NaHCO3 (aq), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customcondensed

Sources & evidence

ORD record
ord-e28e563902e84b93bd7311a1fd4c2b57
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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