Potassium Sodium Tartrate → (6-(Aminomethyl)pyridin-3-YL)methanol

HRID 2355285Notes

Reaction equation

HRID 2355285 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]=[N+]=[N-])=[N:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[NH2:11][CH2:10][C:7]1[N:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 22565575Methyl 6-(azidomethyl)nicotinate

Product 1

HCID 23021825(6-(Aminomethyl)pyridin-3-YL)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add 6-azidomethyl-nicotinic acid methyl ester (2.3 g, 11.97 mmol) and tetrahydrofuran (100 mL) in a flask and cool to 0° C. Add 1M lithium aluminum hydride solution in tetrahydrofuran (17.95 mL, 17.95 mmol) slowly. Stir the mixture for 30 min. Quench the reaction with ice. Add 10 mL of saturated Rochelle's salt solution. Stir for 30 min. Filter, remove the solvent under reduced pressure to give 6-aminomethyl-pyridin-3-yl-methanol (1.6 g, 97% yield) as a yellow oil.

Workup

  1. customQuench
  2. customthe reaction with ice
  3. stirringStir for 30 min
  4. filtrationFilter
  5. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-46a2a8432a054448b5cf5c2664c6726b
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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