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Water → (4-Amino-2-trifluoromethylphenyl)(4-methylpyridin-2-yl)methanol

HRID 856612
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HRID 856612 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

HCID 22938510(4-Amino-2-trifluoromethylphenyl)(4-methylpyridin-2-yl)methanol수율 80.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6e182b5deb8b49e48f6c951ea182d770
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262185B2

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