Citric Acid → Methyl 2-amino-4-methoxy-3-methylbenzoate

HRID 1443453Notes

Reaction equation

HRID 1443453 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](=O)([O-])[O-].[K+].[K+].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[C:10]([CH3:11])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 591654242-Amino-4-methoxy-3-methylbenzoic acid

Product 1

HCID 59165444Methyl 2-amino-4-methoxy-3-methylbenzoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-4-methoxy-3-methyl benzoic acid (3.1 g, 17.1 mmol) in dry DMF (40 ml) was added potassium carbonate (2.4 g, 17.1 mmol) and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (3.1 g, 22 mmol) was added and the mixture was stirred for three hours at room temperature. A 5% aqueous solution of citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with water, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by column chromatography on silica gel eluted with hexane-ethyl acetate which gave the title compound (2.75 g).

Workup

  1. stirringthe mixture was stirred for three hours at room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was isolated by column chromatography on silica gel
  7. washeluted with hexane-ethyl acetate which

Sources & evidence

ORD record
ord-5b59fa71eab14bf78dd0a83c8aa88759
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…