(E)-4-Methyl-6-(prop-1-enyl)pyridin-2-amine → 4-Methyl-6-propylpyridin-2-amine

HRID 1396468Notes

Reaction equation

HRID 1396468 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH3:10])[N:5]=[C:4]([NH2:11])[CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([NH2:11])[CH:3]=1

Participants

4

Reactant 1

HCID 42625452(E)-4-Methyl-6-(prop-1-enyl)pyridin-2-amine

Product 1

HCID 98555244-Methyl-6-propylpyridin-2-amineYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-4-methyl-6-(prop-1-enyl)pyridin-2-amine (235 mg, 1.59 mmol) in ethanol (5.29 mL) was added 10% palladium on carbon (169 mg, 159 μmol). The reaction mixture was evacuated and back filled with H2 three times. The mixture was stirred under an atmosphere of hydrogen (balloon at 1 atm) for 16 h, then filtered through a pad of celite. The filtrate was collected, concentrated in vacuo and purified by chromatography (silica, 30 to 60% ethyl acetate in hexanes gradient) to give 4-methyl-6-propylpyridin-2-amine (135 mg, 899 μmol, 57%) as a colorless oil. MS (EI/CI) m/z: 150.8 [M+H].

Workup

  1. customThe reaction mixture was evacuated
  2. additionback filled with H2 three times
  3. filtrationfiltered through a pad of celite
  4. customThe filtrate was collected
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (silica, 30 to 60% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-ddd8c7695adf4d47950f9953d4081dae
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

Loading…