Hydrochloric Acid → HCID 68288281, compound

HRID 1618909Notes

Reaction equation

HRID 1618909 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:23][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([O:13][C:7]2[CH:8]=[N:9][C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([F:1])[C:11]=3[F:12])[C:17]=1[C:15](=[O:16])[CH3:14]

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 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.5 g of 7,8-difluoro-3-hydroxyquinoline was dissolved in 10 mL of dimethylformamide. 0.52 g of 2,6-difluoroacetophenone and 0.46 g of potassium carbonate were added to the solution, and the mixture was stirred for 2.5 hours at 100° C. The thus obtained reaction solution was poured into ice water and then neutralized with dilute hydrochloric acid, the liquid was separated with ethyl acetate. The organic layer was concentrated and purified by silica gel column chromatography to obtain 0.38 g of 1-[2-fluoro-6-(7,8-difluoroquinolin-3-yloxy)-phenyl]-ethanone (Compound Number 391).

Workup

  1. customThe thus obtained reaction solution
  2. customthe liquid was separated with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-73d11618810544659ae0695cfaf467ba
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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