4-(7-Chloroquinolin-4-yl)butyn-1-ol → 4-(7-Chloroquinolin-4-yl)butan-1-ol
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).