Ethanol → 3-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

HRID 1108402Notes

Reaction equation

HRID 1108402 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([OH:16])[CH:8]=1)[CH3:2].[NH4+].[Cl-].CCO>[Fe].O>[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH:16])[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 54189784Ethyl 3-hydroxy-4-nitrocinnamate

Product 1

HCID 540473973-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a stirred suspension of 11-2 (4.64 g, 19.6 mmol), NH4Cl (524 mg, 9.8 mmol), EtOH (140 mL) and H2O (70 mL) was added iron dust (2.72 g, 48.9 mmol). The resulting yellow suspension was refluxed for 1.5 h., and then the solution was filtered while hot through celite. The filtrate was concentrated and the residue was partitioned between EtOAc and brine. The layers were separated and the EtOAc layer dried (Na2SO4) and concentrated to give 11-3 which was used without further purification in the next step.

Workup

  1. temperatureThe resulting yellow suspension was refluxed for 1.5 h.
  2. filtrationthe solution was filtered while hot through celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between EtOAc and brine
  5. customThe layers were separated
  6. dry with materialthe EtOAc layer dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give 11-3 which
  9. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-2649e4909ed3444b87b1e6d3622b382d
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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