Water → HCID 11183484, compound

HRID 856631Notes

Reaction equation

HRID 856631 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[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]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[OH:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 113449352-(4-Fluorobenzoyl)-6-methylpyridine

Product 1

HCID 11183484HCID 11183484, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(4-fluorobenzoyl)-6-methylpyridine (2.0 g) and sodium azide (3.36 g) in DMSO (40 ml) and the mixture was stirred for 24 hours at 90° C. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and a solution of the residue (1.88 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (0.60 g) in. THF (20 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, and water (0.6 ml), 15% aqueous solution of sodium hydroxide (0.6 ml) and water (1.8 ml) were sequentially and slowly added dropwise to the solution at 0° C. The mixture was stirred at room temperature for 4 days, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration (Celite). The reaction mixure was concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate), to give (4-aminophenyl)(6-methylpyridin-2-yl)methanol (1.44 g) as pale yellow crystals.

Workup

  1. extractionthe mixture was extracted with diethylether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additiona solution of the residue (1.88 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (0.60 g) in
  6. customat 0° C
  7. additionslowly added dropwise to the solution at 0° C
  8. stirringThe mixture was stirred at room temperature for 4 days
  9. additionmagnesium sulfate was added to the mixture
  10. customthe precipitates were removed by filtration (Celite)
  11. concentrationThe reaction mixure was concentrated under reduced pressure
  12. customthe obtained residue was separated
  13. custompurified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-a8eae77bbe7440a7a27137c700b14c6e
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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