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

HRID 1357858Notes

Reaction equation

HRID 1357858 reaction equation
C1(C)C=CC=CC=1NC1[O:9][C:10]2[CH:16]=[C:15]([CH2:17][CH2:18]C(NC3C=CC([C@H](C)CC(O)=O)=CC=3)=O)[CH:14]=[CH:13][C:11]=2[N:12]=1.C([O-])=[O:36].[NH4+].[CH2:39]([OH:41])[CH3:40]>[Pd]>[NH2:12][C:11]1[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:41][CH2:39][CH3:40])=[O:36])=[CH:16][C:10]=1[OH:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 69532998HCID 69532998, 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 ethyl 3-hydroxy4-nitrophenylacetate (5.0 g, Reference Example 6) 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-de3899decf9244938581d3f401b34dbf
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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