Water → Methyl 4-amino-2-nitrobenzoate

HRID 2103817Notes

Reaction equation

HRID 2103817 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[C:14](=O)([O-])[O-].[Na+].[Na+].O.C(OCC)(=O)C>CN(C)C=O.CI>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2357134-Amino-2-nitrobenzoic Acid

Product 1

HCID 14730691Methyl 4-amino-2-nitrobenzoateYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolvent

Procedure

To a suspension of 4-amino-2-nitrobenzoic acid (200 mg, 1.10 mmol) synthesized in accordance with the synthesis method described in WO96/35666 and sodium carbonate (349 mg, 3.29 mmol) in dimethylformamide (5.5 mL), methyl iodide (0.21 ml) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, and extraction was carried out with ethyl acetate, and the combined organic layer was washed with a saturated ammonium chloride aqueous solution and a saturated sodium chloride aqueous solution, followed by drying over anhydrous sodium sulfate. By concentrating the obtained organic layer, 216 mg of the desired product was obtained as a yellow solid (yield 100%).

Workup

  1. customsynthesized in accordance with the synthesis method
  2. additionwas added
  3. washthe combined organic layer was washed with a saturated ammonium chloride aqueous solution
  4. dry with materialby drying over anhydrous sodium sulfate
  5. concentrationBy concentrating the obtained organic layer

Sources & evidence

ORD record
ord-cd6934a949284ac980ec879fd2ddecd7
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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