N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide → N-[2-(3,3-dimethylbutyl)phenyl]acetamide

HRID 1359942Notes

Reaction equation

HRID 1359942 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13].[H][H]>CO.[Pd]>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 58792458N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 58792456N-[2-(3,3-dimethylbutyl)phenyl]acetamideYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.23 g (15 mmol) of N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide (XIII-1) were initially charged in 40 ml of methanol. 0.5 g of palladium-on-carbon (5%) was added, and the mixture is then hydrogenated in an autoclave at a hydrogen pressure of 4 bar for 20 h. Removal of the catalyst and the solvent gave 3.1 g (94% of theory) of N-[2-(3,3-dimethylbutyl)phenyl]acetamide of logP (pH 2.3)=2.69.

Workup

  1. customRemoval of the catalyst

Sources & evidence

ORD record
ord-32ba8bf34fbd4dcb9972a69ed0983ca7
Source dataset
uspto-grants-2011_02
Patent number
US07879760B2

Reaction notes

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