2-Amino-5-methoxy-4-methylbenzoic acid → 2-Amino-5-hydroxy-4-methylbenzoic acid

HRID 1157444Notes

Reaction equation

HRID 1157444 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12]C)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>I>[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 1

HCID 212914972-Amino-5-methoxy-4-methylbenzoic acid

Product 1

HCID 588242352-Amino-5-hydroxy-4-methylbenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

2-Amino-5-methoxy-4-methylbenzoic acid (2.7 g, 14.9 mmol, 61%) and aqueous hydriodic acid (40%, 80 mL) were heated at reflux for 36 h. The aqueous was evaporated under vacuum and the residue washed with ether to yield 2-amino-5-hydroxy-4-methylbenzoic acid (INTERMEDIATE V.1) (2.5 g, 14.9 mmol 100%)

Workup

  1. temperatureat reflux for 36 h
  2. customThe aqueous was evaporated under vacuum
  3. washthe residue washed with ether

Sources & evidence

ORD record
ord-7ca3f52abfb0491b85fd4405e7dcd31b
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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