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

HRID 1669390Notes

Reaction equation

HRID 1669390 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13](=[O:28])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([O:26]C)=[O:25])[CH:17]=1.[OH-].[Na+]>CO>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13](=[O:28])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 673484364-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone

Product 1

HCID 673469134-hydroxy-3-[3-[3-(carboxymethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinoneYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 0.50 g of 4-hydroxy-3-[3-[3-[(methoxycarbonyl)methoxy]phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone and 15 ml of methanol was added dropwise 15 ml of a 1 N aqueous sodium hydroxide solution under ice-cooling. After stirred for 1 hour under ice-cooling, this was concentrated under reduced pressure. The resulting residue was acidified by addition of 2 N hydrochloric acid under ice-cooling, and precipitated crystals were filtered, and washed with tetrahydrofuran to obtain 0.46 g of 4-hydroxy-3-[3-[3-(carboxymethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone [Compound No. (9e)] as a yellow crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationthis was concentrated under reduced pressure
  4. additionThe resulting residue was acidified by addition of 2 N hydrochloric acid under ice-
  5. temperaturecooling
  6. customprecipitated crystals
  7. filtrationwere filtered
  8. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-e47815dc0c7f4600a2090820312d30c5
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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