7-Bromo-5-chloro-2,3-dihydropyrano(4,3,2-de)quinoline → 7-Bromo-2,3-dihydropyrano[4,3,2-de]quinoline

HRID 1627921Notes

Reaction equation

HRID 1627921 reaction equation
[Br:1][C:2]1[C:11]2[C:6]3=[C:7]([CH2:13][CH2:14][O:15][C:5]3=[CH:4][CH:3]=1)[CH:8]=[C:9](Cl)[N:10]=2>FC(F)(F)C(O)=O.[Zn]>[Br:1][C:2]1[C:11]2[C:6]3=[C:7]([CH2:13][CH2:14][O:15][C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][N:10]=2

Participants

4

Reactant 1

HCID 595784977-Bromo-5-chloro-2,3-dihydropyrano(4,3,2-de)quinoline

Product 1

HCID 595785317-Bromo-2,3-dihydropyrano[4,3,2-de]quinolineYield 24.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 7-bromo-5-chloro-2,3-dihydropyrano[4,3,2-de]quinoline (0.220 g; 0.773 mmol) in trifluoroacetic acid (7.5 ml) was added zinc dust (0.253 g; 3.87 mmol) and the reaction was stirred at room temperature for 16 h. The suspension was filtered, concentrated under reduced pressure, diluted with a solution of sodium hydroxide 1N and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulphate and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane furnished 0.047 g (24%) of 7-bromo-2,3-dihydropyrano[4,3,2-de]quinoline as a white solid.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with a solution of sodium hydroxide 1N
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane

Sources & evidence

ORD record
ord-caabc5d515ad4fc2afb867cb771dda2b
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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