4-(4-(2-Quinolinylmethyloxy)styryl)benzonitrile → 4-(4-(2-Quinolinylmethyloxy)phenethyl)benzonitrile

HRID 2073883Notes

Reaction equation

HRID 2073883 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH:17]=[CH:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.[H][H]>C(O)C.[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 542953234-(4-(2-Quinolinylmethyloxy)styryl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 149950044-(4-(2-Quinolinylmethyloxy)phenethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.75 g (2.07 mmol) of (4-(4-(2-quinolinylmethyloxy)styryl)benzonitrile and 0.08 g of 10% Pd on carbon in 75 ml of ethanol is shaken for 1.5 hours under 30 PSI of hydrogen. The mixture is filtered through a bed of celite and the filtrate concentrated in vacuo. Trituration with ether gives a precipitate which is filtered off and recrystallized from methylene chloride-ether to give 4-(4-(2-quinolinylmethyloxy)phenethyl)benzonitrile. (M.P. 156° C.-158° C.)

Workup

  1. filtrationThe mixture is filtered through a bed of celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customTrituration with ether gives a precipitate which
  4. filtrationis filtered off
  5. customrecrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-a8b69b11fe27439892842099d862044e
Source dataset
uspto-grants-1990_04
Patent number
US04920133

Reaction notes

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