Ethanol → 6,7,8,9-Tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one

HRID 1292069노트

반응식

HRID 1292069 반응식
[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[C:5](=[O:15])[NH:4][N:3]=1.O.C(O)C.S(=O)(=O)(O)O>[Pd].C(O)(=O)C>[CH3:1][C:2]1[C:14]2[N:13]3[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)=[CH:7][C:6]=2[C:5](=[O:15])[NH:4][N:3]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 157133114-methyl-2H-pyridazino[4,5-b]indolizine-1-one

생성물 1

HCID 867526156,7,8,9-Tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

4-Methylpyridazino[4,5-b]indolizin-1-one (5.08 g, 25.5 mmol) was hydrogenated at room temperature and 55 psi using a Parr apparatus in a mixture containing 100 mL each of water, ethanol and acetic acid, 3 mL of concentrated sulfuric acid, and 10% Pd on charcoal (500 mg). A white precipitate was observed. The precipitate and catalyst were filtered through Solka Floc and the solids were washed with methanol and methylene chloride. The washes were evaporated to give 6,7,8,9-tetrahydro-4-(methyl)pyridazino[4,5-b]indolizin-1-one (XI). The reduction filtrate was evaporated in vacuo to remove most of the volatiles, then filtered to isolate additional XI. The aqueous phase was then washed with methylene chloride to extract the remaining XI. The product from all three fractions was combined and dried in vacuo to give 3.2 g (67%) of XI.

후처리

  1. customwas hydrogenated at room temperature
  2. filtrationThe precipitate and catalyst were filtered through Solka Floc
  3. washthe solids were washed with methanol and methylene chloride
  4. customThe washes were evaporated

출처 및 근거

ORD 기록
ord-070493017eb640598261d9eabad26bb1
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756501

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