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

HRID 856588ノート

反応式

HRID 856588 の反応式
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

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 11241368HCID 11241368、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-336f00c7d9a64d3196fdd94bfce7bf1f
出典データセット
uspto-grants-2007_08
特許番号
US07262185B2

反応ノート

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