2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Chloroisoquinolin-1(2H)-one

HRID 2277591Notes

Reaction equation

HRID 2277591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 217796976-Chloroisoquinolin-1(2H)-oneYield 60.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-3,4-dihydro-2H-isoquinolin-1-one (181.5 mg, 1 mmol, intermediate A-2) and DDQ (227 mg, 1 mmol) in dioxane (3 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was treated with satd. aq. NaHCO3 solution, and then extracted with ethyl acetate (2×10 mL). The organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo to afford a crude product which was then purified by silica gel flash chromatography to give title compound (108 mg, 60%) as a white solid. MS: 180.0 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. additionthe reaction mixture was treated with satd
  3. extractionaq. NaHCO3 solution, and then extracted with ethyl acetate (2×10 mL)
  4. customThe organic layers were dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customto afford a crude product which
  8. customwas then purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-b89328687a254522841fc18e5b893c07
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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