2-Aminopyridine → 6-Methyl-N-2-pyridinyl-2-pyridinemethanamine

HRID 1926537Notes

Reaction equation

HRID 1926537 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]1[N:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH3:15][C:13]1[N:14]=[C:9]([CH2:8][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 707376-Methyl-2-pyridinecarboxaldehyde

Product 1

HCID 120323576-Methyl-N-2-pyridinyl-2-pyridinemethanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask were added 1.9 g of 2-aminopyridine, 2.4 g of 6-methyl-2-pyridinecarboxaldehyde and 45 ml toluene. The flask was equipped with a Dean-Stark trap and heated to reflux under nitrogen. After 16 hours, the toluene was removed and 40 ml ethanol were added followed by 0.83 g of sodium borohydride. The mixture was stirred at 22 C under nitrogen for 1 hour, and then 30 ml of water were added slowly. Following removal of the ethanol, 60 ml 1M hydrochloric acid was added cautiously, and the aqueous layer was washed with 20 ml ethyl acetate. After basifying with aqueous ammonium hydroxide, the product was extracted with 50 ml ethyl acetate and the solvent was removed. The product was purified by silica gel chromatography using 74% ethyl acetate, 24% hexane, and 2% methanol resulting in 1.5 g of a yellow oil that solidified on standing.

Workup

  1. customThe flask was equipped with a Dean-Stark trap
  2. temperatureheated
  3. temperatureto reflux under nitrogen
  4. customthe toluene was removed
  5. addition40 ml ethanol were added
  6. addition30 ml of water were added slowly
  7. customremoval of the ethanol, 60 ml 1M hydrochloric acid
  8. additionwas added cautiously
  9. washthe aqueous layer was washed with 20 ml ethyl acetate
  10. extractionthe product was extracted with 50 ml ethyl acetate
  11. customthe solvent was removed
  12. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-75bf4e103bb1489d970436c59ef39375
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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