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

HRID 2102507Notes

Reaction equation

HRID 2102507 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-4abe320b4f884a029b0a3476933562b4
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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