Methanol → Methyl 2-Amino-5-methylbenzoate

HRID 1655461Notes

Reaction equation

HRID 1655461 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[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]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 1201104Methyl 2-Amino-5-methylbenzoateYield 74%

Procedure

A mixture of 2-amino-5-methyl benzoic acid (10 g) in methanol (50 ml) containing conc. sulfuric acid (5.5 ml) was heated for 19 hours under reflux. The solvent was distilled off, and the residue was dissolved in water. The solution was neutralized with an aqueous sodium hydroxide, followed by extraction with ethyl acetate. The organic layer was dried and concentrated to afford a pale brown oil (8.1 g, 74%).

Workup

  1. temperaturewas heated for 19 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in water
  5. extractionfollowed by extraction with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9eeb6ffbdf344ea9b75711c75380d678
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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