Ammonium formate → Ethyl 2-(4-amino-3-hydroxyphenyl)acetate

HRID 49702Notes

Reaction equation

HRID 49702 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23508320Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate

Product 1

HCID 23508323Ethyl 2-(4-amino-3-hydroxyphenyl)acetateYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 3-hydroxy-4-nitrophenylacetate (5.0 g, Reference Example 4) was dissolved in ethanol (approximately 200 mL) was treated with ammonium formate (approximately 20 g). The mixture was warmed to 50° C. and then treated cautiously with palladium on charcoal (approximately 1 g, 5%)—effervescence was observed. After 30 minutes the mixture was filtered hot through a pad of celite and the filtrate was concentrated to give the title compound (3.3 g) as a black solid.

Workup

  1. filtrationAfter 30 minutes the mixture was filtered hot through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2f21c1783ad945c5b97ae8938d3780b8
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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