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

HRID 969309Notes

Reaction equation

HRID 969309 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-094d41c2fa9049fe97c2e8c91cd01ea4
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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