Potassium Hydroxide → Brequinar Analog

HRID 2118652노트

반응식

HRID 2118652 반응식
[CH3:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=O.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:27])[C:21]2=O.[OH-:29].[K+]>C(O)C.O>[C:8]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:5]([C:3]2[C:2]([CH3:1])=[C:21]([C:22]([OH:27])=[O:29])[C:20]3[C:24](=[CH:25][CH:26]=[C:18]([F:17])[CH:19]=3)[N:23]=2)=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 95230p-PhenylpropiophenoneHCID 2365665-Fluoroisatin

생성물 1

HCID 1543Brequinar Analog수율 42.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

4-Phenylpropiophenone (18.9 g, 0.09 mole) and 5-fluoroisatin (20 g, 0.09 mole) were suspended in 360 ml of ethanol and stirred mechanically as a solution of 35.2 g KOH in 100 ml water was added dropwise over 15 minutes. The reaction mixture was heated at reflux for 12 hours, cooled, and the ethanol evaporated under reduced pressure. The resulting yellow solid was dissolved in water and washed with ethyl ether. The aqueous layer was cooled to 5° and acidified with glacial acetic acid. The resulting yellow precipitate was filtered and dried. Recrystallization from 200 ml of dimethylformamide and 25 ml water provided 13.8 g of 2-(4-biphenylyl)-6-fluoro-3-methylquinoline-4-carboxylic acid as a white solid, m.p. 303°-306°(d).

후처리

  1. additionwas added dropwise over 15 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 12 hours
  4. temperaturecooled
  5. customthe ethanol evaporated under reduced pressure
  6. dissolutionThe resulting yellow solid was dissolved in water
  7. washwashed with ethyl ether
  8. temperatureThe aqueous layer was cooled to 5°
  9. filtrationThe resulting yellow precipitate was filtered
  10. customdried
  11. customRecrystallization from 200 ml of dimethylformamide and 25 ml water

출처 및 근거

ORD 기록
ord-64f51a43b2a44630980313546e7e05d1
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04680299

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