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

HRID 1264618Notes

Reaction equation

HRID 1264618 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O>CO.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 1

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

Product 1

HCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 4-hydroxy-3-nitrophenylacetate (52.2 g, 0.247 mol) was dissolved in methanol (400 ml) and the resultant solution was then hydrogenated at 5 bar over a 5% w/w palladium on carbon catalyst. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. Trituration with hexane gave methyl 3-amino-4-hydroxyphenylacetate (43.4 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-218ae4610f2e4a5a96fa9a970cbbcb38
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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