Piperidine → 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

HRID 1669389Notes

Reaction equation

HRID 1669389 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O)=[O:4].[C:15]([C:18]1[C:19](=[O:29])[NH:20][C:21]2[C:26]([C:27]=1[OH:28])=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:17])[CH3:16].N1CCCCC1>N1C=CC=CC=1>[OH:28][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:15](=[O:17])[CH:16]=[CH:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH:8]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1494380Methyl 2-(3-formylphenoxy)acetateHCID 546825123-Acetyl-2,4-dihydroxyquinoline

Product 1

HCID 673484364-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinoneYield 67.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 1.43 g of 3-[(methoxycarbonyl)methoxy]benzaldehyde, 0.50 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone and 6 ml pyridine was added 0.1 ml of piperidine, and this was heated under reflux for 1 hour. After cooled to room temperature, precipitated crystals were filtered, and washed with tetrahydrofuran to obtain 0.63 g of 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (7e)] as a yellow crystal.

Workup

  1. temperaturethis was heated
  2. temperatureunder reflux for 1 hour
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-101657a9c98346db952dc23842f87c67
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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