2-Aminonicotinic acid → (2-Aminopyridin-3-yl)methanol

HRID 1761059Notes

Reaction equation

HRID 1761059 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 729302-Aminonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11159325(2-Aminopyridin-3-yl)methanolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminonicotinic acid (20.5 g, 148.1 mmole) in THF was added lithium aluminum hydride (300 mL, 1.0 M in THF) over 30 minutes. The reaction solution was heated to reflux for 18 hrs and then was cooled to room temperature. The reaction was quenched by the sequential dropwise addition of H2O (11.5 mL); 15% NaOH (11.5 mL), and H2O (34.5 mL). The mixture was stirred for 15 min, then was filtered through celite®, and the filter pad was washed thoroughly with THF followed by 5% CH3OH/CHCl3. The filtrate was concentrated to give the title compound (15.24 g. 83%) as a waxy light yellow solid: MS (ES) m/e 125 (M+H)+.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 18 hrs
  3. customThe reaction was quenched by the sequential dropwise addition of H2O (11.5 mL)
  4. filtrationwas filtered through celite®
  5. washthe filter pad was washed thoroughly with THF
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-93f5c59e88f1415baae7aee172e0f4dc
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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