Sodium Hydroxide → 1(6H)-Pyridazinenonanoic acid, 6-oxo-3,4-diphenyl-

HRID 981475Notes

Reaction equation

HRID 981475 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[N:6]=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:3]1.[OH-].[Na+]>CO>[O:1]=[C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:6]=[C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9931844methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoate

Product 1

HCID 100241891(6H)-Pyridazinenonanoic acid, 6-oxo-3,4-diphenyl-Yield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoate (6 g, 14 mmol), 5N NaOH solution (8.6 mL, 43 mmol) and methanol (100 mL) was heated to reflux on a steam bath. After 30 minutes, the mixture was concentrated, diluted with water and acidified to pH=1 with 2N HCl solution. The mixture was extracted with CH2Cl2, the combined extracts dried over sodium sulfate and concentrated to leave an oil that crystallized on standing. Recrystallization from a mixture of CH2Cl2 and hexanes gave 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoic acid (3.92 g, 67%) mp 100°-103° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath
  3. concentrationthe mixture was concentrated
  4. additiondiluted with water
  5. extractionThe mixture was extracted with CH2Cl2
  6. dry with materialthe combined extracts dried over sodium sulfate
  7. concentrationconcentrated
  8. customto leave an oil that
  9. customcrystallized
  10. customRecrystallization
  11. additionfrom a mixture of CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-4ebc8029707b4a02b6aaca8aaaed7544
Source dataset
uspto-grants-1991_02
Patent number
US04992439

Reaction notes

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