Water → HCID 22938510, compound

HRID 856612

Reaction equation

HRID 856612 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])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[N-:21]=[N+]=[N-].[Na+].O>CS(C)=O>[NH2:21][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])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 229385262-(4-Fluoro-2-trifluoromethylbenzoyl)-4-methylpyridine

Product 1

HCID 22938510HCID 22938510, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

2-(4-fluoro-2-trifluoromethylbenzoyl)-4-methylpyridine (4.5 g) and sodium azide (1.3 g) were suspended in dimethylsulfoxide (30 ml), and the mixture was heated with stirring overnight under nitrogen atmosphere at 90° C. 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 evaporated. The residue was dissolved in tetrahydrofuran (30 ml), and to the solution was added aluminum lithium hydride (1.2 g) under ice-cooling, and the mixture was stirred for 1 hour under nitrogen atmosphere under ice-cooling. Water (1.2 ml), 15% aqueous solution of sodium hydroxide (1.2 ml) and water (3.6 ml) were added to the mixture, and the mixture was stirred, dried over anhydrous magnesium sulfate, and filtrated. The solvent of the filtrate was distilled off, to give (4-amino-2-trifluoromethylphenyl)(4-methylpyridin-2-yl)methanol (3.6 g) as colorless 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. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in tetrahydrofuran (30 ml)
  7. additionto the solution was added aluminum lithium hydride (1.2 g) under ice-
  8. temperaturecooling
  9. stirringthe mixture was stirred for 1 hour under nitrogen atmosphere under ice-
  10. temperaturecooling
  11. additionWater (1.2 ml), 15% aqueous solution of sodium hydroxide (1.2 ml) and water (3.6 ml) were added to the mixture
  12. stirringthe mixture was stirred
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltrated
  15. distillationThe solvent of the filtrate was distilled off

Sources & evidence

ORD record
ord-6e182b5deb8b49e48f6c951ea182d770
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Linked notes

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