3-(8-Isoquinolinyl)-2-propyn-1-ol → 8-Isoquinolinepropanol

HRID 2232724Notes

Reaction equation

HRID 2232724 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]#[C:12][CH2:13][OH:14])[CH:4]=[CH:3][N:2]=1>C(O)C.CO.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][CH2:13][OH:14])[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 1

HCID 143474813-(8-Isoquinolinyl)-2-propyn-1-ol

Product 1

HCID 143474828-IsoquinolinepropanolYield 33.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 0.4 g of 3-(8-isoquinolinyl)-2-propyn-1-ol in a mixture of 10 mL of ethanol and 5 mL of methanol was hydrogenated over 0.06 g 10% Pd/C at room temperature and atmospheric pressure for 22 hours andthen at 50 psi for 20 hours. After the catalyst was removed by filtration and the filtrate was concentrated, the residual oil was purified by HPLC (methanol-chloroform; 1:19) and crystallized from ethyl acetate-hexane to yield 0.136 g of 8-isoquinolinepropanol, mp 66°-69° C.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residual oil was purified by HPLC (methanol-chloroform; 1:19)
  4. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d161d1ea037e4601ac79337e1c20b169
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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