Sodium sulfate decahydrate → (2-Aminopyridin-3-yl)methanol

HRID 2238677Notes

Reaction equation

HRID 2238677 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:13][CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 729302-Aminonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11159325(2-Aminopyridin-3-yl)methanolYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 mL of tetrahydrofuran solution containing 5.7 g of lithium aluminum hydride, 20 mL of tetrahydrofuran solution containing 13.8 g of 2-aminonicotinic acid was added, and heated for 2 hours under reflux. After cooling the reaction mixture back to room temperature, sodium sulfate decahydrate was slowly added until there are no bubbles, and stirred for 2 hours at room temperature. The insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and 10.7 g of (2-aminopyridin-3-yl)methanol [147-1] was obtained as a white solid.

Workup

  1. additionwas added
  2. temperatureheated for 2 hours
  3. temperatureunder reflux
  4. filtrationThe insolubles were filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9e4b61e01224bca8e40918421a8d2f1
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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