Acetic Acid → 3-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid ethyl ester

HRID 1976884Notes

Reaction equation

HRID 1976884 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH3:24])=[CH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[N+:21]([O-])=O)[CH3:6]>[Fe].O>[CH2:5]([O:7][C:8](=[O:25])[C:9]([CH3:24])=[CH:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[NH2:21])[CH3:6]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 702169653-(4,5-Dimethoxy-2-nitrophenyl)-2-methyl-2-propenoic acid ethyl ester

Product 1

HCID 702131123-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid ethyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Into 250 ml of glacial acetic acid, 19.0 g of 3-(4,5-dimethoxy-2-nitrophenyl)-2-methyl-2-propenoic acid ethyl ester were dissolved; and, with 15.0 g of iron powder and 20 ml of ion-exchanged water being added thereto, the mixture was refluxed under heating for 40 minutes. The resulting reaction liquid was filtered out, the filtrate was concentrated under a reduced pressure, and thus obtained residue was dissolved in ethyl acetate. The resulting solution was successively washed with water, a 5% aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. After this ethyl acetate solution was left on sodium sulfate anhydride for one night so as to be dried, ethyl acetate was evaporated under a reduced pressure, and the resulting residue was recrystallized from a mixed liquid of hexane/ethanol, whereby 12.5 g of the aimed product were obtained (yield: 78%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 40 minutes
  3. customThe resulting reaction liquid
  4. filtrationwas filtered out
  5. concentrationthe filtrate was concentrated under a reduced pressure, and thus obtained residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washThe resulting solution was successively washed with water
  8. waitAfter this ethyl acetate solution was left on sodium sulfate anhydride for one night so as
  9. customto be dried
  10. customethyl acetate was evaporated under a reduced pressure
  11. customthe resulting residue was recrystallized from a mixed liquid of hexane/ethanol

Sources & evidence

ORD record
ord-f4382da73b27488c94f44b2bf11cf074
Source dataset
uspto-grants-2001_05
Patent number
US06229020B1

Reaction notes

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