Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

HRID 2076263Notes

Reaction equation

HRID 2076263 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 DMF (1 L) mixture of 3-hydroxy-4-nitrobenzoic acid (199 g) and potassium carbonate (450 g) at room temperature. The reaction liquid was stirred overnight at room temperature, to which methyl iodide (230 g) was further added, followed by additionally stirring the reaction liquid at room temperature for 6 hours. The reaction liquid was added to ice water, followed by collecting the precipitated solid by filtration. The resultant solid was dried overnight at 50° C. to provide 178 g of the title compound. The physical property values thereof agreed with reported values (CAS#5081-37-8).

Workup

  1. customThe reaction liquid
  2. additionwas further added
  3. customthe reaction liquid at room temperature for 6 hours
  4. customThe reaction liquid
  5. customby collecting the precipitated solid
  6. filtrationby filtration
  7. customThe resultant solid was dried overnight at 50° C.

Sources & evidence

ORD record
ord-2a0c0f1a8e144d258ac67fdde007807d
Source dataset
uspto-grants-2011_04
Patent number
US07923563B2

Reaction notes

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