Sodium Hydroxide → 4-hydroxy-3-[3-[3-(carboxymethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

HRID 1669367Notes

Reaction equation

HRID 1669367 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10](=[O:25])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([O:23]C)=[O:22])[CH:14]=1.[OH-].[Na+]>CO>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10](=[O:25])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]([OH:23])=[O:22])[CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1363442444-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone

Product 1

HCID 1363442454-hydroxy-3-[3-[3-(carboxymethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinoneYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.42 g of 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone in 10 ml of methanol was added 10 ml of a 1 N aqueous sodium hydroxide solution. After stirred at room temperature for 6 hours, the solvent was distilled off under reduced pressure, this was acidified with 1 N hydrochloric acid, and precipitated crystals were filtered, washed with water, washed with tetrahydrofuran, and then dried to obtain 0.31 g of 4-hydroxy-3-[3-[3-(carboxymethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (9a)] as a yellow crystal.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customprecipitated crystals
  3. filtrationwere filtered
  4. washwashed with water
  5. washwashed with tetrahydrofuran
  6. customdried

Sources & evidence

ORD record
ord-286be2883db04ec69480b2077e67360b
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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