Sodium Hydroxide → HCID 66875499, compound

HRID 2381487Notes

Reaction equation

HRID 2381487 reaction equation
Cl[C:2]1[C:3](=[O:16])[NH:4][N:5]=[CH:6][C:7]=1[N:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].[H][H]>[Pd].O>[CH3:15][N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:7]1[CH:6]=[N:5][NH:4][C:3](=[O:16])[CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 66875192HCID 66875192, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66875499HCID 66875499, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A pressure vial containing a mixture of 4-chloro-5-(methyl-phenyl-amino)-2H-pyridazin-3-one (158.7 mg, 0.67 mmol), water (10 mL), and a 2N aqueous solution of sodium hydroxide (0.37 mL) was treated with 10% palladium on carbon (15.8 mg, 10% weight of 4-chloro-5-(methyl-phenyl-amino)-2H-pyridazin-3-one). The reaction was then pressurized with hydrogen (50 psi), where it shook overnight. The resulting reaction mixture was filtered through a pad of diatomaceous earth and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solution was acidified to pH 1-2 with a 1N aqueous hydrochloric acid solution and then extracted into methylene chloride (2×25 mL). Thin layer chromatography indicated the presence of starting material. The reaction was re-exposed to the same hydrogenation conditions. The reaction was hydrogenated (50 psi) for 2 d. After this time, the resulting reaction mixture was filtered through a pad of diatomaceous earth and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solution was acidified to pH 1-2 with a 1N aqueous hydrochloric acid solution and then extracted into methylene chloride (3×25 mL). The combined organics were dried over magnesium sulfate, filtered, rinsed, and concentrated in vacuo. Silica gel column chromatography (AnaLogix 24 g, 50-100% ethyl acetate/hexanes) afforded 5-(methyl-phenyl-amino)-2H-pyridazin-3-one (75.8 mg, 56%) as a yellow solid.

Workup

  1. additionA pressure vial containing
  2. customThe resulting reaction mixture
  3. filtrationwas filtered through a pad of diatomaceous earth
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. extractionextracted into methylene chloride (2×25 mL)
  7. customfor 2 d
  8. customAfter this time, the resulting reaction mixture
  9. filtrationwas filtered through a pad of diatomaceous earth
  10. washrinsed with methanol
  11. concentrationThe filtrate was concentrated in vacuo
  12. extractionextracted into methylene chloride (3×25 mL)
  13. dry with materialThe combined organics were dried over magnesium sulfate
  14. filtrationfiltered
  15. washrinsed
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02b9e3af377d43e888ff820e1afd86b4
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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