Water → Methyl 2-amino-4,6-dimethoxybenzoate

HRID 749186Notes

Reaction equation

HRID 749186 reaction equation
S(OC)(O[CH3:5])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH2:14][C:15]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[C:16]=1[C:17]([OH:19])=[O:18].O>CN(C)C=O>[NH2:14][C:15]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[C:16]=1[C:17]([O:19][CH3:5])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 116584562-Amino-4,6-dimethoxybenzoic acid

Product 1

HCID 11550253Methyl 2-amino-4,6-dimethoxybenzoateYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl sulfate (1.04 ml, 11.0 mmol) was added dropwise to a mixture of potassium carbonate (3.34 g, 24.2 mmol) and 2-amino-4,6-dimethoxybenzoic acid (2.56 g, 11.0 mmol) in dimethylformamide (70 ml) at 0° C. The reaction was stirred for 1 hour, then poured into water. The resulting precipitate was filtered, washed with water and dried in vacuo. The filtrate was extracted with ethyl acetate, and the combined organic extracts were dried (magnesium sulphate) and concentrated in vacuo. The combined solids were dried in vacuo to yield methyl 2-amino-4,6-dimethoxybenzoate (1.8 g, 77% yield) as a yellow crystalline solid:

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  6. concentrationconcentrated in vacuo
  7. customThe combined solids were dried in vacuo

Sources & evidence

ORD record
ord-14b32e1043484065b85d5420862f40b1
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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