HCID 11011939, compound → HCID 10946429, compound

HRID 2379267Notes

Reaction equation

HRID 2379267 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2/[C:5]/1=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:3])[CH3:2]>O1CCCC1.CC#N.CC#N.Cl[Pd]Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2/[C:5]/1=[CH:14]/[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 11011939HCID 11011939, compound

Product 1

HCID 10946429HCID 10946429, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.2 g of (E)-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)isoquinoline and 8.7 mg of dichlorobis(acetonitrile)palladium(II) in 10 ml of dry tetrahydrofuran was heated at reflux for 7 hours under argon. The yellow solution was evaporated at 15 mbar and the residue was dissolved in diethyl ether. In order to separate the catalyst, the ether solution was filtered through a thin layer of silica gel. After evaporation of the filtrate there was obtained 0.19 g of (Z)-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)-isoquinoline with a m.p. of 101-102° C.; content according to GC 96%:

Workup

  1. temperatureat reflux for 7 hours under argon
  2. customThe yellow solution was evaporated at 15 mbar
  3. dissolutionthe residue was dissolved in diethyl ether
  4. customIn order to separate the catalyst
  5. filtrationthe ether solution was filtered through a thin layer of silica gel
  6. customAfter evaporation of the filtrate there

Sources & evidence

ORD record
ord-14a74a7bb2f14b8bbac431ea7a748792
Source dataset
uspto-grants-1994_11
Patent number
US05360908

Reaction notes

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