Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 1481310Notes

Reaction equation

HRID 1481310 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].[C:14](Cl)(=O)C(Cl)=O.CO>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

6

Reactant 3

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

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 93.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the solution of 2-chloro-3-nitrobenzoic acid (1 g, 4.96 mmol), DMF (0.02 ml, 0.258 mmol) in DCM (20 mL) at 0° C. was added dropwise oxalyl chloride (0.478 ml, 5.46 mmol). The reaction was warmed to rt after the addition. After 3 h, methanol (10 mL) was added dropwise to the reaction mixture and the reaction was stirred at rt for 18 h and then the reaction was concentrated. The residue was dissolved in dichloromethane and passed through a plug of silica gel eluting with a 50% ethyl acetate/n-hexanes mixture. The filtrate was concentrated in vacuo to give the title compound as a white solid (1 g, 93% yield). MS (ESI) m/z: 216.0 (M+H)+.

Workup

  1. additionafter the addition
  2. concentrationthe reaction was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3a62dc4ae78f4a4b94cb69603d6c6a14
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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