HCID 53889779, compound → HCID 23465869, compound

HRID 443819Notes

Reaction equation

HRID 443819 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 1

HCID 53889779HCID 53889779, compound

Product 1

HCID 23465869HCID 23465869, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-Methoxyvinyl)isoquinoline (a mixture of the cis and trans isomers; 5 g) is dissolved in methanol (50 cc). A catalyst (3% palladium-on-carbon; 0.5 g) is added and the mixture is hydrogenated in an autoclave at 20° C. under a pressure of 15 atmospheres for 20 hours, whilst stirring. The reaction mixture is then filterred and the filtrate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg). The oily residue is dissolved in methylene chloride (10 cc) and the solution is poured into a column (diameter 2 cm) containing silica (100 g) in methylene chloride. Elution is carried out with a 99-1 (by volume) methylene chloridemethanol mixture (2 liters), 100 cc fractions being collected. Fractions 10 to 15 are combined and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg). 3-(2-Methoxyethyl)isoquinoline (2.1 g) is obtained in the form of an oil.

Workup

  1. concentrationthe filtrate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg)
  2. dissolutionThe oily residue is dissolved in methylene chloride (10 cc)
  3. additionthe solution is poured into a column (diameter 2 cm)
  4. additioncontaining silica (100 g) in methylene chloride
  5. washElution
  6. custombeing collected
  7. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg)

Sources & evidence

ORD record
ord-c6d3c482e6ff49ee9dc8738daa50cc65
Source dataset
uspto-grants-1981_04
Patent number
US04261992

Reaction notes

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