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

HRID 412477Notes

Reaction equation

HRID 412477 reaction equation
CC1ON=C(C(NC(C2C=CC(N[C:22](=[O:41])[CH2:23][C:24]3[CH:40]=[CH:39][C:27]4[N:28]=C(NC5C=CC=CC=5C)[O:30][C:26]=4[CH:25]=3)=CC=2)CC(O)=O)=O)C=1.C([O-])=[O:43].[NH4+].[CH2:46](O)[CH3:47]>[Pd]>[NH2:28][C:27]1[CH:39]=[CH:40][C:24]([CH2:23][C:22]([O:41][CH2:46][CH3:47])=[O:43])=[CH:25][C:26]=1[OH:30]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 18537741HCID 18537741, 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-hydroxy-4-nitrophenylacetate (5.0 g, Reference Example 3) 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-b25c282322354b2bb06d322f242aab87
Source dataset
uspto-grants-2003_05
Patent number
US06562851B2

Reaction notes

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