Methyl 2-(4-hydroxy-3-nitrophenyl)acetate → Methyl 2-(3-amino-4-hydroxyphenyl)acetate

HRID 48148

Reaction equation

HRID 48148 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([NH2:12])[CH:6]=1

Participants

4

Reactant 1

HCID 1473109Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

Product 1

HCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetateYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl(4-hydroxy-3-nitrophenyl)acetate [from step 3] (48.9 g, 0.23 mole) and 5% palladium on carbon were suspended in methanol and the resulting mixture was hydrogenated until all the starting material had been consumed. The reaction mixture was filtered to remove the catalyst and the filtercake was washed with methanol. The combined filtrate and washings were concentrated in vacuo, affording methyl(3-amino-4-hydroxyphenyl)acetate as a solid (41.0 g).

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. washthe filtercake was washed with methanol
  5. concentrationThe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-7084f53764894ab79b3924f11ea5a968
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Linked notes

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