4-Nitrophenol → 3-(2-Aminophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

HRID 2269789Notes

Reaction equation

HRID 2269789 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([CH3:13])[C:10]([OH:12])=[O:11].[CH:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16](O)[CH:15]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CC=CN=1)C.ClCCl>[N+:20]([C:19]1[CH:14]=[CH:15][C:16]([O:11][C:10](=[O:12])[C:9]([CH3:13])=[CH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH2:1])=[CH:17][CH:18]=1)([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672452723-(2-Aminophenyl)-2-methyl-2-propenoic acid

Product 1

HCID 702154653-(2-Aminophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into 20 ml of dichloromethane, 0.19 g (1.1 mmol) of (E) 3-(2-aminophenyl)-2-methyl-2-propenoic acid and 0.18 g of p-nitrophenol (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved; and 10 mg of dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were added thereto. Further, while the mixture was stirred under cooling with ice, 0.41 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC-HCl) (manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto in portions. The mixture was returned to room temperature and then was stirred for 20 hours. After the end point of this reaction was verified by TLC, the reaction liquid was concentrated under a reduced pressure and then was dissolved in 100 ml of ethyl acetate. This solution was washed several times with a 5% aqueous sodium hydrogencarbon ate solution and then with a saturated aqueous sodium chloride solution, and was dried with magnesium sulfate anhydride. Thereafter, the solvent was evaporated, whereby a crude product was obtained. This product was recrystallized from ethanol, whereby 0.29 g of the aimed compound was obtained as a crystal (yield: 91%).

Workup

  1. additionwas added
  2. customwas returned to room temperature
  3. stirringwas stirred for 20 hours
  4. customthe reaction liquid
  5. concentrationwas concentrated under a reduced pressure
  6. dissolutionwas dissolved in 100 ml of ethyl acetate
  7. washThis solution was washed several times with a 5% aqueous sodium hydrogencarbon ate solution
  8. dry with materialwith a saturated aqueous sodium chloride solution, and was dried with magnesium sulfate anhydride
  9. customThereafter, the solvent was evaporated
  10. customwhereby a crude product was obtained
  11. customThis product was recrystallized from ethanol

Sources & evidence

ORD record
ord-00258a0ab0ba46d6aec52e22e406db71
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

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