Ethanol → Ethyl 2-(4-amino-3-hydroxyphenyl)acetate

HRID 1375075Notes

Reaction equation

HRID 1375075 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21](NC2C=CC(C3(CC(O)=O)CC4C(=CC=CC=4)C3)=CC=2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9]C(NC1C=CC=CC=1C)=O.C([O-])=O.[NH4+].[CH2:47]([OH:49])[CH3:48]>[Pd]>[CH2:47]([O:49][C:21](=[O:22])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH2:9])=[C:3]([OH:2])[CH:4]=1)[CH3:48]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 10231423HCID 10231423, compound

Product 1

HCID 23508323Ethyl 2-(4-amino-3-hydroxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
50 °C

Procedure

A solution of (3-hydroxy-4-nitro-phenyl)-acetic acid ethyl ester (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 filter-aid 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
  2. filtrationof filter-aid
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1b8ee275771b496cacd1c009f573fbaa
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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