HCID 66874911, compound → 5-(4-Acetylphenethyl)-3-chloropicolinonitrile

HRID 1259244Notes

Reaction equation

HRID 1259244 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([Cl:20])[C:15]([C:18]#[N:19])=[N:16][CH:17]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pt]=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([Cl:20])[C:15]([C:18]#[N:19])=[N:16][CH:17]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 66874911HCID 66874911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 668922525-(4-Acetylphenethyl)-3-chloropicolinonitrile

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-((4-acetylphenyl)ethynyl)-3-chloropicolinonitrile (from the previous step) (1 eq) in ethanol (0.1 M) was added Platinum Oxide (30 mol %). Hydrogen gas was introduced via a balloon, and the reaction was stirred for 0.5 hour. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated en vaccuo and purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-100% ethyl acetate in hexane to give 5-(4-acetylphenethyl)-3-chloropicolinonitrile as an off-white solid.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated en vaccuo
  4. custompurified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f4c0111efe6b406cb5620051a0d8906c
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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