Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 1698536Notes

Reaction equation

HRID 1698536 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]N(C)C=O.C(Cl)(=O)C(Cl)=O.CO>ClCCl>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 198702-Chloro-3-nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 20 g (99 mmol) of 2-chloro-3-nitrobenzoic acid in 800 mL dichloromethane was cooled in an ice bath. Dimethylformamide (0.40 ml) was added to the reaction mixture followed by dropwise addition of 13.85 g (109 mmol) of oxalyl chloride. The reaction was allowed to warm to room temperature and was stirred for 6 h. Methanol (200 mL) was added dropwise and the reaction was stirred overnight. The solvent was evaporated in vacuo. The residue was triturated with n-hexane. The resulting solid was collected by filtration, washed with hexane and dried in vacuo to give 21.0 g (98%) of the title compound.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated in vacuo
  3. customThe residue was triturated with n-hexane
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3200be7d3607455885fce0cca44cceee
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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