Ethyl 3-hydroxy-4-nitrocinnamate → Ethyl 4-amino-3-hydroxybenzenepropionate

HRID 982226Notes

Reaction equation

HRID 982226 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[H][H]>O1CCCC1.C(O)C.[C].[Pd]>[NH2:15][C:14]1[CH:13]=[CH:12][C:4]([CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][C:2]=1[OH:1]

Participants

6

Reactant 2

HCID 54189784Ethyl 3-hydroxy-4-nitrocinnamateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18008946Ethyl 4-amino-3-hydroxybenzenepropionateYield 105.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran and 130 ml of ethanol was dissolved 3.32 g of ethyl 3-hydroxy-4-nitrocinnamate. To the solution was added 100 mg of 10% palladium-carbon. The mixture was stirred under normal pressure in a hydrogen flow until absorption of hydrogen was discontinued. The catalyst was filtered off by suction and the filtrate was concentrated under reduced pressure to obtain 3.10 g of crude ethyl 4-amino-3-hydroxybenzenepropionate as an oily substance.

Workup

  1. filtrationThe catalyst was filtered off by suction
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7dbc5f8708f743cdb32b45916c25a38d
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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