5-(Prop-1-en-2-yl)pyridin-2-amine → 5-(Propan-2-yl)pyridin-2-amine

HRID 2366072Notes

Reaction equation

HRID 2366072 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)[CH3:3]>CO.[Pd]>[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)[CH3:3]

Participants

4

Reactant 1

HCID 552857655-(Prop-1-en-2-yl)pyridin-2-amine

Product 1

HCID 179858055-(Propan-2-yl)pyridin-2-amineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a Parr flask, a mixture of 1.1 g (8.2 mmol) of 5-(prop-1-en-2-yl)pyridin-2-amine in 40 mL of MeOH and 0.11 g of 10% Pd/C is hydrogenated at 7 bar for 24 hours. The reaction mixture is then filtered through Whatman GF/F paper and concentrated under reduced pressure. 1.07 g of 5-(propan-2-yl)pyridin-2-amine are thus obtained in the form of a yellow oil, which is used without further purification in the following step.

Workup

  1. filtrationThe reaction mixture is then filtered through Whatman GF/F paper
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-457a896bf34a46b59b7b9471b4bd2b7f
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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