Acetic Acid → HCID 16063552, 화합물
반응식
CCO[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:21](O)(=O)[CH3:22]>>[CH2:21]([N:20]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:4](=[O:5])[N:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:22]참가 물질
반응 조건
- 온도
- 120 °C
실험 절차
To a solution of cyclohexanone-2-carboxylic acid ethylester (0.6 g) in acetic acid (1 mL) in a round bottom flask under argon was added phenylhydrazine (0.38 g). The mixture was immersed into an oil bath and heated to 120° C. overnight. The reaction vessel was then cooled and the acetic acid was evaporated in vacuo and the remaining solid was dissolved in EtOAc and water. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo and azeotroped with toluene (2×). The crude residue was then purified via ISCO Combiflash chromatography (eluting with EtOAc/heptane) to afford the desired 2-phenyl-1,2,4,5,6,7-hexahydro-indazol-3-one (0.56 g) as a light brown solid. MS (ESI+): 215.4 ([M+H]+).
후처리
- customThe mixture was immersed into an oil bath
- temperatureThe reaction vessel was then cooled
- customthe acetic acid was evaporated in vacuo
- dissolutionthe remaining solid was dissolved in EtOAc
- customThe phases were separated
- extractionthe aqueous phase was extracted with further EtOAc
- washThe combined organic phases were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customazeotroped with toluene (2×)
- customThe crude residue was then purified via ISCO Combiflash chromatography (eluting with EtOAc/heptane)
출처 및 근거
- ORD 기록
- ord-e904886cc2164d16900bb6da0a188193
- 출처 데이터셋
- uspto-grants-2010_01
- 특허 번호
- US07652057B2
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