Pyridine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

HRID 38309Notes

Reaction equation

HRID 38309 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[NH:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=O.N1C=CC=CC=1.N1CCCCC1>O>[OH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5](=[O:15])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][C:26]([F:27])([F:28])[F:29])=[C:17]([Cl:16])[CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546825123-Acetyl-2,4-dihydroxyquinoline

Product 1

HCID 695121564-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinoneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.60 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 1.99 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 10 ml of pyridine and 88 μl of piperidine was heated under refluxing overnight. After cooling to room temperature, 50 ml of water was added to the reaction mixture, and precipitated crystals were filtered, and washed with 40 ml of tetrahydrofuran, and 60 ml of hexane to obtain 0.92 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (3c-32)] as a yellow crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing overnight
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with 40 ml of tetrahydrofuran, and 60 ml of hexane

Sources & evidence

ORD record
ord-31190487ee7542c5af8bd15daeb36fda
Source dataset
uspto-grants-2013_09
Patent number
US08524729B2

Reaction notes

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