Dimethylformamide → Methyl 3-methoxy-4-nitrobenzoate

HRID 1362585Notes

Reaction equation

[CH3:1]I.O[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])C(O)=O.[C:16](=[O:19])([O-])[O-:17].[K+].[K+].CN([CH:25]=[O:26])C>>[CH3:1][O:17][C:16](=[O:19])[C:6]1[CH:10]=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:4]([O:26][CH3:25])[CH:5]=1

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 dropped to a mixture of 3-hydroxy-4-nitrobenzoic acid (199 g) and potassium carbonate (450 g) in DMF (1 L) at room temperature. After agitating the reaction solution at room temperature overnight, methyl iodide (230 g) was further added to the reaction mixture, and the reaction mixture was further agitated at room temperature for 6 hours. The reaction mixture was added to ice water and the deposited solids were obtained by filtration. 178 g of the title compound was obtained by drying the obtained solid at 50° C. overnight. The physical properties was in agreement with the reported values (CAS#5081-37-8).

Workup

additionwas further added to the reaction mixture
customthe deposited solids were obtained by filtration

Sources & evidence

ORD record: ord-157a615ff32f404fa7d367d009d250d6
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880009B2

Reaction notes

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