Quinoline → Acetic acid 4-(4-methoxy-butyl)-pyridin-3-yl ester

HRID 2263553Notes

Reaction equation

HRID 2263553 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:13][C:14](=[O:16])[CH3:15].N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:13][C:14](=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 66887632Acetic acid 4-(4-methoxy-but-1-ynyl)pyridin-3-yl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 66889070Acetic acid 4-(4-methoxy-butyl)-pyridin-3-yl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of 9.9 mmol acetic acid 4-(4-methoxy-but-1-ynyl)-pyridin-3-yl ester and 0.51 mmol quinoline in 230 ml ethyl acetate is added 0.56 mmol 10% Pd/C. The suspension is vigorously stirred under an atmospheric pressure of hydrogen for 2 hours. The catalyst is removed by filtration and the solvent is evaporated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60 F) and identified based on its Rf value.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-43b236f6ad8c4a5397ece9368d9d1cfb
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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