6-(Quinolin-3-yl)hex-5-yn-1-ol → 6-(Quinolin-3-yl)hexan-1-ol

HRID 1583433Notes

Reaction equation

HRID 1583433 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:2]=1.[H][H]>[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:2]=1

Participants

4

Reactant 2

HCID 135575496-(Quinolin-3-yl)hex-5-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 135575476-(Quinolin-3-yl)hexan-1-ol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-Quinolinehexanol was prepared by reduction of 13.5 g of 6-(3-quinolinyl)-5-hexyn-1-ol over 1.0 g of 10% palladium on carbon at 1 atmosphere of hydrogen. The crude product obtained after filtration and evaporation was chromatographed over silica gel by high pressure liquid chromatography eluting with 2% methanol-dichloromethane. The first product to elute amounted to 0.95 g which was evaporatively distilled to yield 0.76 g (6%) of 6-[3-(1,2,3,4-tetrahydro)quinolinyl]hexanol, bp 180°-185° C./0.1 mm. The second product to elute amounted to 9.1 g which was evaporatively distilled to give 8.3 g (61%) of 3-quinolinehexanol, bp 195°-205° C. 0.25 mm.

Workup

  1. customThe crude product obtained

Sources & evidence

ORD record
ord-c69f2e0d18c74383a64ff4f730f1e685
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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