Hydrochloric Acid → 1,4-Dihydro-1-phenylindeno[1,2-c]pyrazole

HRID 366382

반응식

HRID 366382 반응식
O[CH:2]=[C:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.Cl.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C(O)C>[C:14]1([N:20]2[C:4]3[C:5]4[C:10]([CH2:11][C:3]=3[CH:2]=[N:21]2)=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 60962Phenylhydrazine hydrochlorideHCID 37648821H-Inden-1-one, 2,3-dihydro-2-(hydroxymethylene)-

생성물 1

HCID 108790091,4-Dihydro-1-phenylindeno[1,2-c]pyrazole

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-Hydroxymethlene indan-1-one (Example 1(ii)(a) (6.0 g, 37.5 mmol), phenylhydrazine hydrochloride (Aldrich) (5.48 g, 37.9 mmol), 10 M hydrochloric acid (1 cm3) and ethanol (30 cm3) were stirred under reflux for 19 hours. After cooling, the solvent was evaporated under reduced pressure and the residue dissolved in dichloromethane, then washed with 2M sodium hydroxide. The organic layer was separated, dried (Na2SO4) filtered and concentrated in vacuo. Purification by Kugelrohr distillation afforded an off-white solid (150° C., 0.01 mmHg) m.p. 119-120° C.

후처리

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with 2M sodium hydroxide
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification
  11. distillationby Kugelrohr distillation
  12. customafforded an off-white solid (150° C., 0.01 mmHg) m.p. 119-120° C.

출처 및 근거

ORD 기록
ord-380d35a1d5e1462b8e71bdae12a790df
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130228

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