4-(7-Chloroquinolin-4-yl)butyn-1-ol → 4-(7-Chloroquinolin-4-yl)butan-1-ol

HRID 1274408Notes

Reaction equation

HRID 1274408 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:12][CH2:13][C:14]#[C:15][OH:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 221206664-(7-Chloroquinolin-4-yl)butyn-1-ol

Product 1

HCID 221206674-(7-Chloroquinolin-4-yl)butan-1-olYield 49.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

4-(7-chloroquinolin-4-yl)butyn-1-ol (1 g) was dissolved in ethanol (25 mL) in a Parr hydrogenation bottle and platinum (IV) oxide [Adams' Catalyst] (100 mg) was added. The Parr bottle was placed on a Parr hydrogenation apparatus and the solution hydrogenated at 50 psi for 2 hours after which time the starting material had been judged to be consumed by TLC. The spent catalyst was removed by filtration through a Celite pad and the pad carefully washed with more ethanol. The combined filtrates were evaporated in vacuo and the residue purified by flash chromatography on silica gel (ethyl acetate; then ethyl acetate:methanol, 95:5) to give the title compound (500 mg).

Workup

  1. additionwas added
  2. customto be consumed by TLC
  3. customThe spent catalyst was removed by filtration through a Celite pad
  4. washthe pad carefully washed with more ethanol
  5. customThe combined filtrates were evaporated in vacuo
  6. customthe residue purified by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-10f48641c6c540a9b6230d621781f096
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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