Potassium Carbonate → HCID 86762491, compound

HRID 1618905Notes

Reaction equation

HRID 1618905 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].C[C:20]([C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1F)=[O:21]>C(#N)C>[F:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([O:12][C:8]2[CH:9]=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:22]=1[CH:20]=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 836431-(2,6-Difluorophenyl)ethan-1-oneHCID 682880678-fluoroquinolin-3-ol

Product 1

HCID 86762491HCID 86762491, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After 30 ml of acetonitrile was added to 3.0 g of 8-fluoro-3-hydroxyquinoline, 3.1 g of potassium carbonate and 3.5 g of 2,6-difluoroacetophenone were added. After the reaction solution was heated under reflux for 3 hours, the reaction solution was filtered with CELITE. After the filtrate was extracted with ethyl acetate, the organic layer was concentrated and purified by silica gel column chromatography to obtain 3.0 g of 2-fluoro-6-(8-fluoroquinolin-3-yloxy)-benzaldehyde (Compound Number 341).

Workup

  1. additionwere added
  2. temperatureAfter the reaction solution was heated
  3. temperatureunder reflux for 3 hours
  4. filtrationthe reaction solution was filtered with CELITE
  5. extractionAfter the filtrate was extracted with ethyl acetate
  6. concentrationthe organic layer was concentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7978b09554d24f46b7bef5e1a2d6734c
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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