Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

HRID 1009320Notes

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

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide2×

HCID 11430Potassium Carbonate

HCID 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

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

Sources & evidence

ORD record: ord-9dc7a632cf3f4b05821c073a54e7e516
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973033B2

Reaction notes

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