2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Fluoro-1,2-dihydroquinolin-2-one

HRID 969309노트

반응식

HRID 969309 반응식
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[F:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]2>O1CCOCC1>[F:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]2

참가 물질

4

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 136907656-Fluoro-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 98340436-Fluoro-1,2-dihydroquinolin-2-one수율 31.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

DDQ (0.38 g, 1.7 mmol) was added to a solution of 6-fluoro-3,4-dihydro-1H-quinolin-2-one (0.18 g, 1.1 mmol) in dioxane (25 mL) and the resulting solution was refluxed for 16 h. The mixture was concentrated, and sat aqueous Na2CO3 (25 mL) was added followed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL). The combined organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and purified by flash CC (SiO2; CH2Cl2/MeOH 20:1) to give the title compound (0.056 g, 31%). 1H NMR (DMSO-D6) δ 11.8 (brs, 1H), 7.85 (d, J=9.4 Hz), 7.50 (dd, J=2.8, 9.2 Hz), 7.43-7.37 (m, 1H), 7.37-7.25 (m, 1H), 6.54 (d, J=9.4 Hz).

후처리

  1. temperaturethe resulting solution was refluxed for 16 h
  2. concentrationThe mixture was concentrated
  3. additionwas added
  4. extractionfollowed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL)
  5. dry with materialThe combined organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash CC (SiO2; CH2Cl2/MeOH 20:1)

출처 및 근거

ORD 기록
ord-094d41c2fa9049fe97c2e8c91cd01ea4
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307075B2

반응 노트

불러오는 중…