6-Aminonicotinic acid → (6-Aminopyridin-3-yl)methanol

HRID 492252Notes

Reaction equation

HRID 492252 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][N:9]=1.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 184966-Aminonicotinic acidHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2794829(6-Aminopyridin-3-yl)methanolYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., lithiumaluminium hydride (1.7 g) was added to a THF solution (58 mL) of 6-amino-nicotinic acid (2.0 g), and stirred overnight at room temperature. Sodium sulfate 10 hydrate was added to the reaction liquid at 0° C. to stop the reaction, and this was dried with anhydrous sodium sulfate. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain (6-amino-3-pyridinyl)methanol (1.7 g) as a brown solid.

Workup

  1. customthe reaction
  2. dry with materialthis was dried with anhydrous sodium sulfate
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4caf420ba91a45e2a7267bb03f3d5b30
Source dataset
uspto-grants-2009_05
Patent number
US07531668B2

Reaction notes

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