Methyl 2-hydroxy-3-nitrobenzoate → Methyl 3-amino-2-hydroxybenzoate

HRID 2064750Notes

Reaction equation

HRID 2064750 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:14])([O-])=O>CO.[Pd]>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][CH:13]=[C:4]([NH2:1])[C:5]=1[OH:14]

Participants

4

Reactant 1

HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 12782444Methyl 3-amino-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 3-nitrosalicylate (26.6 mmol) in MeOH (50 mL) is treated with Pd/C (10%, 500 mg) and stirred at RT under a hydrogen atmosphere (1 bar) for 16 h. After filtration through celite and removal of the solvents the desired product is obtained which is used without further purification. LC-MS: tR=0.51 min; [M+H]+=168.0.

Workup

  1. filtrationAfter filtration
  2. customthrough celite and removal of the solvents the desired product
  3. customis obtained which
  4. customis used without further purification

Sources & evidence

ORD record
ord-c7328c4ec9c649a5a8a65fc6aa38421e
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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