Toluene → 2-[2-(7-Methoxy-1-naphthyl)ethenyl]-1H-isoindole-1,3(2H)-dione

HRID 1511162Notes

Reaction equation

HRID 1511162 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH:21]([N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])=[CH2:22].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][CH:8]=[C:7]2[CH:22]=[CH:21][N:23]2[C:24](=[O:33])[C:25]3[C:26](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:28])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 81531DiisopropylethylamineHCID 103577857-Methoxynaphthalen-1-yl trifluoromethanesulfonate

Product 1

HCID 666018072-[2-(7-Methoxy-1-naphthyl)ethenyl]-1H-isoindole-1,3(2H)-dioneYield 80%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a reactor, 2 g of the compound obtained in Step A, 2 eq. of N-vinylphthalimide, 1.25 eq. of diisopropylethylamine and 0.05 eq. of palladium tetrakis(triphenylphosphine) are introduced into toluene and heated at reflux. The reaction is continued at reflux for 12 hours and then the reaction mixture is cooled to ambient temperature. Ethyl acetate is added, and then washings with water and IN HCl solution are carried out. After evaporating off the solvents, the residue obtained is purified by chromatography on silica gel (eluant:dichloromethane/heptane 1/1, and then dichloromethane) to yield the title product in a yield of 80% and with a chemical purity of more than 95%.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureat reflux for 12 hours
  4. washwashings with water
  5. customAfter evaporating off the solvents
  6. customthe residue obtained
  7. customis purified by chromatography on silica gel (eluant

Sources & evidence

ORD record
ord-034d0182b3354cf2b84db7216e1742f9
Source dataset
uspto-grants-2012_07
Patent number
US08212077B2

Reaction notes

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