6-Methylpyridine-2-carbonitrile → (6-Methylpyridin-2-yl)methanamine

HRID 2182169Notes

Reaction equation

HRID 2182169 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[N:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH3:7][C:8]1[N:13]=[C:12]([CH2:14][NH2:15])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 741826-Methylpyridine-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 246721(6-Methylpyridin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 1.0 M LiAlH4 in THF (35.6 mL, 35.6 mmol) at 0° C. was added dropwise a solution of 6-methyl-pyridine-2-carbonitrile I-4h (2.0 g, 16.9 mmol) in THF (34 mL). The reaction mixture was stirred at 0° C. for 5 minutes after the addition was complete and then quenched with the addition of 1N NaOH (20 mL). The resulting reaction mixture was stirred for 1 h and filtered through celite washing well with ether. The filtrate was diluted with 1N NaOH (20 mL) and the organic layer separated. The organic layer was then washed with brine, dried (Na2SO4), and concentrated in vacuo to give the desired product I-4i (1.02 g).

Workup

  1. additionafter the addition
  2. customquenched with the addition of 1N NaOH (20 mL)
  3. customThe resulting reaction mixture
  4. stirringwas stirred for 1 h
  5. filtrationfiltered through celite
  6. washwashing well with ether
  7. additionThe filtrate was diluted with 1N NaOH (20 mL)
  8. customthe organic layer separated
  9. washThe organic layer was then washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a93887fbbb8b41b195111377112dad27
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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