Sodium Sulfate → 6-Dimethylaminomethyl-2-hydroxymethylpyridine

HRID 1702413Notes

Reaction equation

HRID 1702413 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[N:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[CH:7][CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:15][N:2]([CH2:3][C:5]1[N:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 13102909Methyl 6-[(dimethylamino)carbonyl]-2-pyridinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 155923006-Dimethylaminomethyl-2-hydroxymethylpyridineYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-(N,N-dimethylcarbamyl-2-carbomethoxypyridine (20.3 g; 97.5 mmoles) [prepared in Step A] in 200 ml of tetrahydrofuran was added to a suspension of lithium aluminum hydride (9.6 g; 0.25 moles) in 500 ml of tetrahydrofuran. The mixture was stirred and heated at reflux temperature under a nitrogen atmosphere for 3 hours then left at ambient temperature overnight. The mixture was decomposed with a saturated aqueous solution of Na2SO4, filtered, dried and evaporated under reduced pressure. The residue was placed on 275 g of aluminum oxide and eluted with methylene chloride. The appropriate fractions were combined and evaporated to give 5.2 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature under a nitrogen atmosphere for 3 hours
  3. filtrationfiltered
  4. customdried
  5. customevaporated under reduced pressure
  6. washeluted with methylene chloride
  7. customevaporated

Sources & evidence

ORD record
ord-aeb5768334c749d3992046b5b93b809a
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

Loading…