HCID 53694269, compound → HCID 13655191, compound

HRID 745254Notes

Reaction equation

HRID 745254 reaction equation
[C:1]1(=[O:28])[N:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12>C(Cl)(Cl)Cl.[C].[Pd]>[C:4]1(=[O:23])[N:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[C:1](=[O:28])[C:2]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:3]12

Participants

4

Reactant 1

HCID 53694269HCID 53694269, compound

Product 1

HCID 13655191HCID 13655191, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Catalytic reduction of a solution of 9 g of 4-[2-(4-phthalimidomethylphenyl)ethenyl]benzonitrile in 300 ml of chloroform was carried out with 2 g of a 5% palladium-carbon as catalyst. The reaction mixture was filtered from the spent catalyst and the filtrate was concentrated under reduced pressure. Ether was added to the residue and the precipitated crystals were collected by filtration to obtain 8.5 g of 4-[2-(4-phthalimidomethylphenyl)ethyl]benzonitrile; m.p. 194°-197° C.

Workup

  1. filtrationThe reaction mixture was filtered from the spent catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionEther was added to the residue
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-45b993fc34c744619d386f1729e44e36
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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