Methanol → Methyl 2-amino-4-methylbenzoate

HRID 1953125Notes

Reaction equation

HRID 1953125 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 sulphuric 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-eb2798e583254f8f884c8bcc5b4e5efb
Source dataset
uspto-grants-2000_09
Patent number
US06114538

Reaction notes

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