Water → 5-(Aminomethyl)pyridin-2-amine

HRID 1595214Notes

Reaction equation

HRID 1595214 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=O)=[CH:10][N:9]=1.O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([CH2:12][NH2:14])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 95006-AminonicotinamideHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 157667715-(Aminomethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (21 mmol) is added in small portions to 10 mmol of 6-aminonicotinamide in tetrahydrofuran. The mixture is heated at reflux for 72 hours, then brought to ambient temperature and hydrolyzed with water and then with a 1N sodium hydroxide solution. After stirring for one hour, the mixture is filtered through Celite and washed with an 85/15 tetrahydrofuran/methanol mixture. The solvents are then evaporated off and the residue obtained is purified by chromatography on silica gel to yield the expected product in the form of a white solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 72 hours
  3. filtrationthe mixture is filtered through Celite
  4. washwashed with an 85/15 tetrahydrofuran/methanol mixture
  5. customThe solvents are then evaporated off
  6. customthe residue obtained
  7. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bfb930d4f0744a3f9f2f422afb06d341
Source dataset
uspto-grants-2001_09
Patent number
US06288077B1

Reaction notes

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