Ethanol → 8-Chloro-2-methyl-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine

HRID 236725

반응식

HRID 236725 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH:15]=O)[CH:14]=[C:10]3[C:9](=[O:17])[NH:8][CH:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.CCO.O.NN>C1COCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH3:15])[CH:14]=[C:10]3[C:9](=[O:17])[NH:8][CH:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 123778918-Chloro-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-carboxaldehyde

생성물 1

HCID 123778928-Chloro-2-methyl-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine

시약·촉매·용매 1

HCID 21883165Tetrahydrofuran hexane용매

실험 절차

To a solution of 3.43 g. (10.15 mmol) of the end product of Example 15 in 60 ml. of absolute EtOH, was added 12 ml. of hydrazine-hydrate. The reaction was heated to reflux for 17 hours, then cooled and concentrated in vacuo. The residue was taken up in 60 ml. toluene; 1.0 g. potassium t-butoxide added and the mixture heated to reflux for 8 hours, then cooled to room temperature and stirred for 9 hours. The reaction was poured over ice and brine and toluene added. The toluene phase was separated and dried over Na2SO4. The aqueous phase was extracted well with CH2Cl2 and the combined extracts dried over Na2SO4. The dried solutions were combined and concentrated and the crude product recrystallized from THF/hexane to give the desired end product, mp 258°-261°. An analytical sample was prepared by an additional recrystallization from THF/hexane and was obtained as colorless crystals: mp 259°-261°.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 17 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionpotassium t-butoxide added
  6. temperaturethe mixture heated
  7. temperatureto reflux for 8 hours
  8. additionThe reaction was poured over ice and brine and toluene
  9. additionadded
  10. customThe toluene phase was separated
  11. dry with materialdried over Na2SO4
  12. extractionThe aqueous phase was extracted well with CH2Cl2
  13. dry with materialthe combined extracts dried over Na2SO4
  14. concentrationconcentrated
  15. customthe crude product recrystallized from THF/hexane
  16. customto give the desired end product, mp 258°-261°
  17. customwas obtained as colorless crystals

출처 및 근거

ORD 기록
ord-c8b840a86ba84a80a734a72a5dbe24a1
출처 데이터셋
uspto-grants-1979_06
특허 번호
US04157331

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