6-Cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one → 6-cyclopropyl-8-fluoroisoquinolin-1(2H)-one

HRID 2069861Notes

Reaction equation

HRID 2069861 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([F:14])[CH:13]=2)[C:10](=[O:15])[NH:9][CH2:8][CH2:7]3)[CH2:3][CH2:2]1>O1CCOCC1.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([F:14])[CH:13]=2)[C:10](=[O:15])[NH:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 594738126-Cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 594737616-cyclopropyl-8-fluoroisoquinolin-1(2H)-oneYield 33.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound I (0.272 g, 1.32 mmol) in 8 ml dioxane placed in a pressure tube was added under argon DDQ (0.301 g, 1.32 mmol). The tube was sealed and the mixture heated at 100° C. for 18 hours with stirring. After cooling the reaction was diluted with ethyl acetate and the organic phase washed with 1N NaOH and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (75% ethyl actate/hexane to 100% ethyl acetate) to afford 90 mg (33% yield) of II.

Workup

  1. additionwas added under argon DDQ (0.301 g, 1.32 mmol)
  2. customThe tube was sealed
  3. temperatureAfter cooling the reaction
  4. washthe organic phase washed with 1N NaOH and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (75% ethyl actate/hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-408927526109424da17d9bf0939d3998
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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