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

HRID 2069742Notes

Reaction equation

HRID 2069742 reaction equation
[F: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.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[F: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 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 450908026-Fluoroisoquinolin-1(2H)-oneYield 36.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6-Fluoro-3,4-dihydro-2H-isoquinolin-1-one (149 mg, 0.903 mmol) was dissolved in 3 mL 1,4-dioxane. Argon was bubbled through this solution for 1 minute and 2,3-dichloro-5,6-dicyano-p-benzoquinone (205 mg, 0.903 mmol) was added. This was heated at 100° C. for 24 hours. The resulting mixture was partitioned between ethyl acetate and 1M aq. sodium hydroxide. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (50% ethyl acetate/hexanes) to yield 6-Fluoro-2H-isoquinolin-1-one (54 mg, 0.33 mmol). MS (ESI) 164.1 (M+H)−.

Workup

  1. customArgon was bubbled through this solution for 1 minute
  2. customThe resulting mixture was partitioned between ethyl acetate and 1M aq. sodium hydroxide
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-eb69663ddca6470da5cae2dafbf3bc8e
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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