Quinoline → HCID 67808707, compound

HRID 1656313Notes

Reaction equation

HRID 1656313 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](OCC)(=[O:13])[CH3:12]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[N:1]1[CH:2]=[CH:3][CH:4]=[C:5](/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:12][CH2:11][OH:13])[CH:10]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 8857Ethyl Acetate

Product 1

HCID 67808707HCID 67808707, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

A solution of 45 ml (0.47 mol) of 3-bromopyridine and 52 g (0.53 mol) of 5-hexyn-l-ol in 150 ml of triethylamine and 500 ml of dichloromethane is degassed for 15 minutes with argon, and 3 g (4,3 mmol) of bis(triphenylphosphine)palladium(II)chloride and 450 mg of cuprous iodide is added. The mixture is heated at reflux for 3 h. The cooled reaction mixture is diluted with 1 liter of dichloromethane and is washed with water and brine, dried (K2CO3), concentrated and bulb-to-bulb distilled (b.p. 120°-130° C./0.05 mbar), to give 63 g of 6-(3-pyridyl)hex-5-ynol as a yellow oil, which is dissolved in 500 ml of ethyl acetate and af ter addition of 15 ml of quinoline is hydrogenated f or 5 h over 6 g Lindlar catalyst (Pb-poisoned Pd catalyst) in a Parrhydrogenator. The crude product is evaporatively distilled (b.p. 120°-130° C./0.05 mbar), yielding 61 g (73%) of (Z)-6-(3-pyridyl)hex-5-enol as a colourless viscous liquid. (C11H15NO; F.W. 177.3).

Workup

  1. customf or 5 h
  2. distillationThe crude product is evaporatively distilled (b.p. 120°-130° C./0.05 mbar)

Sources & evidence

ORD record
ord-7000ae8abb404e90bc823b0be5a71c6d
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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