Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

HRID 1436077Notes

Reaction equation

HRID 1436077 reaction equation
CI.[OH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7](O)=[O:8].[C:16](=O)([O-])[O-].[K+].[K+].CN([CH:25]=[O:26])C>>[CH3:16][O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([O:26][CH3:25])=[O:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Procedure

Methyl iodide (463 g) was added dropwise to a mixture of 3-hydroxy-4-nitrobenzoic acid (199 g) with potassium carbonate (450 g) in DMF (1 L) at room temperature. The reaction solution was stirred at room temperature overnight, and then methyl iodide (230 g) was added to the reaction solution. The reaction solution was further stirred at room temperature for six hours. The reaction solution was added to ice water, and the precipitated solid was collected by filtration. The resulting solid was dried at 50° C. overnight to obtain 178 g of the title compound. The property values corresponded to the reported values (CAS #5081-37-8).

Workup

  1. stirringThe reaction solution was further stirred at room temperature for six hours
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe resulting solid was dried at 50° C. overnight

Sources & evidence

ORD record
ord-bba303fe13b74221b35a6ff4a69b6e0d
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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