Sodium Hydroxide → FK 838

HRID 703979Notes

Reaction equation

HRID 703979 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=23)=[N:10]1)=[O:5])C.[OH-].[Na+]>O.CO>[C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=23)=[N:10]1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10597233HCID 10597233, compound

Product 1

HCID 3035594FK 838Yield 74.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-[2-(3-ethoxycarbonylpropyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (13.7 g) and sodium hydroxide (2.73 g) in a mixture of water (8.6 ml) and methanol (96 ml) was refluxed for 2 hours and then the solvent was evaporated in vacuo. The residue was dissolved in water, and the aqueous solution was acidified with hydrochloric acid, and extracted with chloroform. The extract was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was recrystallized from a mixture of ethanol and n-hexane to give 3-[2-(3-carboxypropyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (9.48 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was recrystallized from a mixture of ethanol and n-hexane

Sources & evidence

ORD record
ord-2ca22888a3754d069dcc70f33c69733d
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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