Water → α-(4-Aminophenyl)-4-methyl-2-pyridinemethanol

HRID 856588Notes

Reaction equation

HRID 856588 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[N-:17]=[N+]=[N-].[Na+].O>CS(C)=O>[NH2:17][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 11241368HCID 11241368, compound

Product 1

HCID 11333370α-(4-Aminophenyl)-4-methyl-2-pyridinemethanolYield 113%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(4-fluorobenzoyl)-4-methylpyridine (1.6 g) and sodium azide (2.4 g) were suspended in dimethylsulfoxide (15 ml) under nitrogen atmosphere 90° C., and the mixture was heated with stirring overnight. The mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was dissolved in tetrahydrofuran (50 ml), and to the solution was added aluminum lithium hydride (0.66 g) under ice-cooling, and the mixture was stirred overnight at room temperature under nitrogen atmosphere. To the solution were added water (0.66 ml), 15% aqueous solution of sodium hydroxide (0.66 ml) and water (1.98 ml) under ice-cooling, the mixture was stirred and dried over anhydrous magnesium sulfate. After filtration, the solvent of the filtrate was distilled off, to give (4-aminophenyl)(4-methylpyridin-2-yl)methanol (1.8 g) as pale yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  7. additionto the solution was added aluminum lithium hydride (0.66 g) under ice-
  8. temperaturecooling
  9. stirringthe mixture was stirred overnight at room temperature under nitrogen atmosphere
  10. additionTo the solution were added water (0.66 ml), 15% aqueous solution of sodium hydroxide (0.66 ml) and water (1.98 ml) under ice-
  11. temperaturecooling
  12. stirringthe mixture was stirred
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationAfter filtration
  15. distillationthe solvent of the filtrate was distilled off

Sources & evidence

ORD record
ord-336f00c7d9a64d3196fdd94bfce7bf1f
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…