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

HRID 1372594Notes

Reaction equation

HRID 1372594 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)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 4-hydroxy-3-nitrophenylacetate (2.15 g, 10.1 mmol) and 5% palladium/carbon (2.15 g) were suspended in methanol (100 ml). The resulting suspension was subjected to catalytic hydrogenation for 20 hours under stirring at room temperature and normal pressure. The catalyst was then filtered off from the reaction mixture. The filtrate was distilled under reduced pressure to remove the solvent, whereby the title compound (1.72 g, 93%) was obtained as a brown solid (this compound was provided for the subsequent reaction without further purification).

Workup

  1. filtrationThe catalyst was then filtered off from the reaction mixture
  2. distillationThe filtrate was distilled under reduced pressure
  3. customto remove the solvent, whereby the title compound (1.72 g, 93%)
  4. customwas obtained as a brown solid (this compound
  5. customwas provided for the subsequent reaction without further purification)

Sources & evidence

ORD record
ord-cdeb7798aac34171a7d3e2ae329df2a6
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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