HCID 57656020, compound → HCID 57656545, compound

HRID 911665Notes

Reaction equation

HRID 911665 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]#[C:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1>CO.[Pd]>[NH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][C:2]([CH3:14])([CH3:13])[CH3:1])=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 57656020HCID 57656020, compound

Product 1

HCID 57656545HCID 57656545, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve 5-(3,3-dimethyl-but-1-ynyl)-2-cyano-pyridine (255 mg, 1.5 mmol) in methanol (15 mL). Add 10% Pd/C (Degussa type E101, 230 mg) and submit the mixture to hydrogenation under atmospheric pressure (balloon) overnight. Filter the catalyst through Celite® and concentrate the filtrate in vacuo to provide the title compound as a solid (231 mg, 87%) that was used without any further purification. MS (ES+) m/z: 193 (M+H)+.

Workup

  1. customunder atmospheric pressure (balloon) overnight
  2. filtrationFilter the catalyst through Celite®
  3. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-a0093a10d1a1484c9785832b4fa1d184
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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