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

HRID 66234

반응식

HRID 66234 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH2:15][OH:16])[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.C1COCC1>O=[Mn]=O.C1COCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[N:12]=[C:13]([CH:15]=[O:16])[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 2

HCID 8028TetrahydrofuranHCID 123778908-Chloro-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-methanol

생성물 1

HCID 123778918-Chloro-5,6-dihydro-4-oxo-6-phenyl-4H-pyrazolo[1,5-a][1,4]benzodiazepine-2-carboxaldehyde

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 21883165Tetrahydrofuran hexane용매

실험 절차

A solution of 5.85 g. (17 mmol) of the end product of Example 14 in 600 ml. dry THF was mixed with 24 g. of activated MnO2 and heated to reflux for 17 hours. The mixture was cooled, filtered and the collected solids washed thoroughly with THF. The combined filtrate and washings were concentrated in vacuo. Recrystallization of this crude product from THF/hexane yielded the desired end product. An analytical sample was prepared by an additional recrystallization from THF/hexane and was obtained as colorless plate: mp 276°-278°.

후처리

  1. temperatureto reflux for 17 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe collected solids washed thoroughly with THF
  5. concentrationThe combined filtrate and washings were concentrated in vacuo
  6. customRecrystallization of this crude product from THF/hexane
  7. customyielded the desired end product
  8. customwas obtained as colorless plate

출처 및 근거

ORD 기록
ord-45b22a592c164f49b68473621678da58
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04130716

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