Methanol → Methyl 2-amino-4-methylbenzoate

HRID 2257501Notes

Reaction equation

HRID 2257501 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 753164-Methylanthranilic acid

Product 1

HCID 11205965Methyl 2-amino-4-methylbenzoate

Procedure

A mixture of 2-amino-4-methylbenzoic acid (15.0 g) and concentrated suiphuric acid (20 ml) was heated under reflux with methanol for 18 hours. After removal of the solvent the residue was dissolved in dichloromethane, basified with sodium carbonate solution and the organic phase was washed with water, dried (anhydrous magnesium sulphate) and the solvent evaporated to give methyl 2-amino-4-methylbenzoate, m.p. 41°-43° C.

Workup

  1. temperaturewas heated
  2. customAfter removal of the solvent the residue
  3. dissolutionwas dissolved in dichloromethane
  4. washthe organic phase was washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-01c3819e463a4d5aaa44816eefd155d8
Source dataset
uspto-grants-1997_08
Patent number
US05658858

Reaction notes

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