Piperidine → 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

HRID 38305Notes

Reaction equation

HRID 38305 reaction equation
[C:1]([C:4]1[C:5](=[O:12])[NH:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=O.N1CCCCC1>N1C=CC=CC=1.O>[OH:10][C:9]1[CH:8]=[C:7]([CH3:11])[NH:6][C:5](=[O:12])[C:4]=1[C:1](=[O:3])[CH:2]=[CH:17][C:16]1[CH:19]=[CH:20][C:21]([O:22][C:23]([F:24])([F:25])[F:26])=[C:14]([Cl:13])[CH:15]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 546761542(1H)-Pyridinone, 3-acetyl-4-hydroxy-6-methyl-

Product 1

HCID 1363673444-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinoneYield 36.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.50 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone, 0.74 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 6 mg of pyridine and 0.1 ml of piperidine was heated under refluxing for 4 hours. After cooled to room temperature, 40 ml of water was added to the reaction mixture, precipitated crystals were filtered, and this was washed with tetrahydrofuran, then with ethyl acetate to obtain 0.41 g of 4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (3a-32)] as a yellow crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 4 hours
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washthis was washed with tetrahydrofuran

Sources & evidence

ORD record
ord-92d980da2a324de2b436ae444770958c
Source dataset
uspto-grants-2013_09
Patent number
US08524729B2

Reaction notes

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