3-Hydroxyquinoline → HCID 23503311, compound

HRID 2422424Notes

Reaction equation

HRID 2422424 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 h. After cooling the reaction mixture was filtered through a short celite pad. The filtrate was concentrated to provide compound 51 (2.07 g, quant.) as a brown oil. 1H NMR (300 MHz/CDCl3) δ 7.02 (1H, d, J=9.1 Hz), 7.61 (1H, m), 7.72-7.80 (3H, m), 8.10-8.18 (2H, m), 8.45 (1H, d, J=2.7 Hz), 8.82 (1H, d, J=2.8 Hz).

Workup

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

Sources & evidence

ORD record
ord-c2130894c4ff49159708f54812154d44
Source dataset
uspto-grants-2011_06
Patent number
US07960408B2

Reaction notes

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