1-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole → 2-Fluoro-4-(1,2,4-triazol-1-yl)phenylamine

HRID 2299206

반응식

HRID 2299206 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:3][C:2]=1[F:1]

참가 물질

4

반응물 1

HCID 218839191-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole

생성물 1

HCID 218838662-Fluoro-4-(1,2,4-triazol-1-yl)phenylamine수율 64.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

1-(3-Fluoro-4-nitrophenyl)-1H-1,2,4-triazole (3.06 g) was dissolved in ethanol (100 ml) and admixed with 10% Pd/C (50% water, 612 mg) and then stirred under a hydrogen atmosphere at room temperature for 1 hour. After filtering the catalyst off, the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the resultant solution as washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:2). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield 1-(4-amino-3-fluorophenyl)-1H-1,2,4-triazole (1.68 g) as yellow powdery crystals.

후처리

  1. filtrationAfter filtering the catalyst off, the filtrate
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washthe resultant solution as washed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:2)
  8. concentrationA desired fraction was concentrated under reduced pressure
  9. customthe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

출처 및 근거

ORD 기록
ord-b70b8a07105d416b8fe25803d4567585
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495604B1

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