Water → (2-Aminopyridin-3-yl)methanol

HRID 82900

Reaction equation

HRID 82900 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1.O.[Na]>C1COCC1>[NH2:7][C:8]1[C:13]([CH2:14][OH:15])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 729302-Aminonicotinic acidHCID 5360545SodiumHCID 21226445Aluminium lithium hydride

Product 1

HCID 11159325(2-Aminopyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (12.4 g, 326.7 mmol) was portionwisely added to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217.2 mmol) in THF (350 mL) at 0° C. Once the addition was completed, the reaction mixture was stirred at room temperature for 15 minutes and then at reflux overnight. The mixture was then cooled to 0° C. and hydrolyzed by the successive addition of water (18 mL), a solution of sodium hydroxyde (18 mL) and water (30 mL) again. The resulting white suspension was filtered on Clarcel® and the cake was washed with THF (200 mL) and a mixture of CHCl3/MeOH (250 mL, 9:1). After concentration to dryness of the filtrate, the title product was obtained as a yellow solid (24.2 g, 90%).

Workup

  1. additionOnce the addition
  2. temperatureat reflux overnight
  3. filtrationThe resulting white suspension was filtered on Clarcel®
  4. washthe cake was washed with THF (200 mL)
  5. additiona mixture of CHCl3/MeOH (250 mL, 9:1)
  6. concentrationAfter concentration to dryness of the filtrate

Sources & evidence

ORD record
ord-212e7e6947c5488984cdbd83e5ff1afa
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Linked notes

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