3-Hydroxyquinoline → HCID 23503311, compound

HRID 1835518Notes

Reaction equation

HRID 1835518 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cl:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1[O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 113763-HydroxyquinolineHCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 23503311HCID 23503311, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-hydroxyquinoline (1.00 g) and 3-chloro-4-fluoronitrobenzene (1.21 g) in Acetone (20 ml), was added K2CO3 (2.86 g). The mixture was refluxed for 1 hr. After cooling the reaction mixture was filtered through a short celite pad. The filtrate was concentrated to provide compound 198 (2.07 g, quant.) as a brown oil.

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. temperatureAfter cooling the reaction mixture
  3. filtrationwas filtered through a short celite pad
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0789f53e720e41eeb6e1cd5b53663956
Source dataset
uspto-grants-2004_08
Patent number
US06770648B2

Reaction notes

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