Water → 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

HRID 1669366Notes

Reaction equation

HRID 1669366 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].[CH3:13][O:14][C:15]([CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)=[O:16].O>N1C=CC=CC=1.N1CCCCC1>[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:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][CH2:17][C:15]([O:14][CH3:13])=[O:16])[CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1494380Methyl 2-(3-formylphenoxy)acetateHCID 546761542(1H)-Pyridinone, 3-acetyl-4-hydroxy-6-methyl-

Product 1

HCID 1363442444-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinoneYield 31.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

In a mixture of 9 ml of pyridine and 150 μl of piperidine were dissolved 0.75 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone and 0.75 g of 3-[(methoxycarbonyl)methoxy]benzaldehyde, and the solution was heated under reflux for 4 hours. After cooled to room temperature, 20 ml of water was added, precipitated crystals were filtered, washed with water, washed with tetrahydrofuran, and dried to obtain 0.42 g of 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (7a)] as a yellow crystal.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 4 hours
  3. customprecipitated crystals
  4. filtrationwere filtered
  5. washwashed with water
  6. washwashed with tetrahydrofuran
  7. customdried

Sources & evidence

ORD record
ord-32d9537e238849e8b72f5cd4bcbf8d9d
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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