Hydrazine hydrate (1:1) → 6-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one

HRID 1971900

반응식

HRID 1971900 반응식
C([O:3][C:4](=O)[CH:5](O)[CH:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)[C:7](=O)[CH2:8][CH2:9][CH2:10][CH3:11])C.O.[NH2:29][NH2:30]>C(O)(=O)C>[CH2:8]([C:7]1[C:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][CH:14]=2)=[CH:5][C:4](=[O:3])[NH:29][N:30]=1)[CH2:9][CH2:10][CH3:11]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 673757473-(4-Cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

생성물 1

HCID 673752856-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of the octanoic acid ethyl ester (105 mmol, 39.5 g) in glacial acetic acid (25.5 mL) was added hydrazine hydrate (525 mmol, 25.5 mL), and the reaction was heated at 100° C. for 12 h. After cooling, the volatiles were removed in vacuo, the residue was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), saturated NaHCO3 (3×100 mL), brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate (200 mL) and hexanes (300 mL) to afford 6-butyl-5-(4-cyclohexyloxy-phenyl)-2H-pyridazin-3-one.

후처리

  1. temperatureAfter cooling
  2. customthe volatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (300 mL)
  4. washThe organic layer was washed with water (100 mL), saturated NaHCO3 (3×100 mL), brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from a mixture of ethyl acetate (200 mL) and hexanes (300 mL)

출처 및 근거

ORD 기록
ord-13fbcb4e18c04e66b853b2bcdb0dafdf
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431575B2

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