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

HRID 2269768Notes

Reaction equation

HRID 2269768 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 product was successively washed with water, a 5% aqueous sodium hydrogencarbon ate solution, and a saturated aqueous sodium chloride solution; and then was left on sodium sulfate anhydride for one night so as to be dried. Ethyl acetate was evaporated under a reduced pressure from this solution, and the resulting crude product was recrystallized from 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 product was successively washed with water
  8. waitand then was left on sodium sulfate anhydride for one night so as
  9. customto be dried
  10. customEthyl acetate was evaporated under a reduced pressure from this solution
  11. customthe resulting crude product was recrystallized from hexane/ethanol

Sources & evidence

ORD record
ord-4c889f57288741eb805a246cf407934c
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

Loading…