2-Aminopyridine → HCID 12221910, compound

HRID 1926517Notes

Reaction equation

HRID 1926517 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=O>C1(C)C=CC=CC=1>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 12221910HCID 12221910, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask were added 4.7 g of 2-aminopyridine, 5.35 g of 2-pyridinecarboxaldehyde, and 75 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 100 ml ethanol were added followed by 2.1 g of sodium borohydride. The mixture was stirred at 22 C under nitrogen for 1 hour, and then 50 ml of water were added slowly. Following removal of the ethanol, aqueous ammonium chloride was cautiously added resulting in gas evolution. The product was extracted twice with 50 ml ethyl acetate and washed with 30 ml water. After solvent removal, the product was purified by silica gel chromatography using 5% methanol in ethyl acetate resulting in an orange oil.

Workup

  1. customThe flask was equipped with a Dean-Stark trap
  2. temperatureheated
  3. temperatureto reflux under nitrogen
  4. customthe toluene was removed
  5. addition100 ml ethanol were added
  6. addition50 ml of water were added slowly
  7. customremoval of the ethanol, aqueous ammonium chloride
  8. additionwas cautiously added
  9. customresulting in gas evolution
  10. extractionThe product was extracted twice with 50 ml ethyl acetate
  11. washwashed with 30 ml water
  12. customAfter solvent removal
  13. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-28258f6c8ac845a29ce4c67c2242e682
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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