4-Nitrophenol → 3-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

HRID 2269770Notes

Reaction equation

HRID 2269770 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH:12]=[C:13]([CH3:17])[C:14]([OH:16])=[O:15].[CH:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20](O)[CH:19]=1.CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C>CCCCCC.C(OCC)(=O)C.ClCCl>[N+:24]([C:23]1[CH:18]=[CH:19][C:20]([O:15][C:14](=[O:16])[C:13]([CH3:17])=[CH:12][C:3]2[CH:4]=[C:5]([O:10][CH3:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=2[NH2:1])=[CH:21][CH:22]=1)([O-:26])=[O:25]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 702156293-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid

Product 1

HCID 702156313-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Into 20 ml of dichloromethane, 0.82 g (3.5 mmol) of (E) 3-(2-amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid and 0.97 g (7 mmol) of p-nitrophenol (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved, and 40 mg of dimethylaminopyridine (manufactured by Wako Pure Chemical Industries, Ltd.) were added thereto. While this mixture was stirred under cooling with ice, 0.81 g (4.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC/HCl) (manufactured by Wako Pure Chemical Industries, Ltd.) were added thereto in portions. The mixture was returned to room temperature and then was stirred for 20 hours. After the end point of the reaction was verified by TLC, the reaction liquid was concentrated under a reduced pressure and then was dissolved in 100 ml of ethyl acetate. After this solution was washed and dried, the solvent was evaporated, whereby a syrupy crude product was obtained. This product was refined by a silica gel column chromatography (n-hexane/ethyl acetate=2/1), whereby 0.15 g of the aimed compound was obtained as a yellow crystal (yield: 12%).

Workup

  1. additionwere 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. washAfter this solution was washed
  8. customdried
  9. customthe solvent was evaporated
  10. customwhereby a syrupy crude product was obtained

Sources & evidence

ORD record
ord-db11790bc2424578b84ee861ea2b8e46
Source dataset
uspto-grants-2001_12
Patent number
US06329546B1

Reaction notes

Loading…