Water → 2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-one

HRID 257372

반응식

HRID 257372 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][NH2:11].CC[O:14][C:15]([CH:17]1[C:22](=O)[CH2:21][CH2:20][CH2:19][CH2:18]1)=O.O>C1(C)C=CC=CC=1.C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:15](=[O:14])[C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=2[NH:11]1

참가 물질

6

반응물 3

HCID 962WaterHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 44203045(2-Fluoro-4-methoxyphenyl)hydrazine

생성물 1

HCID 189810182-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매2회

실험 절차

To a solution of 6.28 g (0.040 mole) of 2-fluoro-4-methoxyphenylhydrazine in 200 mL of toluene was added with stirring 6.82 g (0.040 mole) of ethyl 2-cyclohexanonecarboxylate. This mixture was heated at reflux under a nitrogen atmosphere while water was removed with a Dean-Stark trap. When all water had been removed, the reaction mixture was cooled, and the solvent was evaporated under reduced pressure, leaving a residue which was then dissolved in acetic acid. This solution was heated at reflux for approximately sixteen hours, after which the solvent was evaporated under reduced pressure, leaving a residue. This residue was dissolved in toluene, which was also evaporated under reduced pressure. The residue was dissolved in ethyl acetate and placed on a silica gel column and eluted with ethyl acetate. An attempt to crystallize the product by dissolving it in diethyl ether after the ethyl acetate had been evaporated was unsuccessful. After the solvent had been evaporated from this product, it was again heated at reflux in acetic acid for 24 hours and allowed to cool to room temperature, where the solution stirred for an additional 48 hours. The solvent was evaporated under reduced pressure, leaving a residue weighing 4.32 g. Two additional fractions weighing 0.80 g and 2.75 g had been recovered by extracting the reaction mixture before the solvent was evaporated. The NMR spectrum of the residue showed it to be a mixture of 2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-one and the 2-fluoro-4-methoxyphenylhydrazone of 2-cyclohexanonecarboxylic acid.

후처리

  1. temperatureThis mixture was heated
  2. customwas removed with a Dean-Stark trap
  3. customWhen all water had been removed
  4. temperaturethe reaction mixture was cooled
  5. customthe solvent was evaporated under reduced pressure
  6. customleaving a residue which
  7. temperatureThis solution was heated
  8. temperatureat reflux for approximately sixteen hours
  9. customafter which the solvent was evaporated under reduced pressure
  10. customleaving a residue
  11. customwhich was also evaporated under reduced pressure
  12. dissolutionThe residue was dissolved in ethyl acetate
  13. washeluted with ethyl acetate
  14. customAn attempt to crystallize the product
  15. dissolutionby dissolving it in diethyl ether after the ethyl acetate
  16. customhad been evaporated
  17. customAfter the solvent had been evaporated from this product, it
  18. temperaturewas again heated
  19. temperatureat reflux in acetic acid for 24 hours
  20. customThe solvent was evaporated under reduced pressure
  21. customleaving a residue
  22. customhad been recovered
  23. extractionby extracting the reaction mixture before the solvent
  24. customwas evaporated
  25. additiona mixture of 2-(2-fluoro-4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazol-3-one

출처 및 근거

ORD 기록
ord-311ea8ab56d54c818b1e6ba41abaf56e
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262390

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