Hydrochloric Acid → HCID 68288281, compound

HRID 1618902Notes

Reaction equation

HRID 1618902 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7]([OH:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]([C:17]1[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1F)=[O:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH:6]=[C:7]([O:13][C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=3[C:15](=[O:16])[CH3:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 836431-(2,6-Difluorophenyl)ethan-1-oneHCID 682855737,8-difluoroquinolin-3-ol

Product 1

HCID 68288281HCID 68288281, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

After 0.91 g of 7,8-difluoro-3-hydroxyquinoline and 0.94 g of 2,6-difluoroacetophenone were dissolved in 10 ml of dimethylformamide, 0.9 g of potassium carbonate was added. The reaction solution was heated to 100° C. and the mixture was stirred for 4.5 hours. Dilute hydrochloric acid was added to the reaction solution and the solution was separated by ethyl acetate. The organic layer was concentrated and purified by silica gel column chromatography to obtain 0.64 g of 1-[2-(7,8-difluoroquinolin-3-yloxy)-6-fluoro-phenyl]-ethanone (Compound Number 391).

Workup

  1. customthe solution was separated by ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a64240117c1e436db68c1a153d19a78f
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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