Sodium Hydroxide → HCID 54262608, compound

HRID 2185817Notes

Reaction equation

HRID 2185817 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH:6]=[CH:7][CH2:8][N:9]2[C:14](=[O:15])[C:13]([C:16]([O:18]C)=[O:17])=[CH:12][C:11]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:10]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:16]([C:13]1[C:14](=[O:15])[N:9]([CH2:8][CH:7]=[CH:6][C:5]2[CH:28]=[CH:29][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:10]=[C:11]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:12]=1)([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53962849HCID 53962849, compound

Product 1

HCID 54262608HCID 54262608, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-(4-chlorocinnamyl)-4-methoxycarbonyl-6-(4-methoxyphenyl)-2H-pyridazin-3-one (1.35 g, 3.29 mmol) in methanol (50 ml), a 4N aqueous solution of sodium hydroxide (20 ml) was added at room temperature, followed by stirring at the same temperature for 30 minutes. The methanol was distilled off under reduced pressure, and water (100 ml) was added to the residue. The mixture was acidified with hydrochloric acid under ice-water cooling, followed by extraction with chloroform. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby the title compound (1.30 g, 99.7%) was obtained as yellow crystals.

Workup

  1. distillationThe methanol was distilled off under reduced pressure, and water (100 ml)
  2. additionwas added to the residue
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-457798b04a164042b295021efba2c0c0
Source dataset
uspto-grants-2002_06
Patent number
US06403586B1

Reaction notes

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