Sodium Hydroxide → HCID 54742209, compound

HRID 2427784Notes

Reaction equation

HRID 2427784 reaction equation
Br[C:2]1[C:3](=[O:17])[N:4]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=2)[N:5]=[CH:6][C:7]=1[OH:8].[OH-].[Na+]>C(O)C.[Pd]>[F:16][C:11]1[CH:10]=[C:9]([N:4]2[C:3](=[O:17])[CH:2]=[C:7]([OH:8])[CH:6]=[N:5]2)[CH:14]=[C:13]([F:15])[CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67148004HCID 67148004, compound

Product 1

HCID 54742209HCID 54742209, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Bromo-2-(3,5-difluorophenyl)-5-hydroxypyridazin-3-one (0.6 g, 1.98 mmoles) was dissolved in ethanol (50 ml) and 1M sodium hydroxide (4 ml) was added. 10% Palladium on carbon (0.15 g) was added and the flask was placed under an atmosphere of hydrogen (balloon) with stirring. The reaction mixture was stirred overnight at room temperature. Filtered off the catalyst using Hyflo and evaporated to dryness. Added 2M hydrochloric acid and extracted into ethyl acetate. Washed with water and dried over anhydrous magnesium sulphate. Filtered and evaporated the filtrate to give a white solid. Triturated with diethyl ether to give the product as a white solid. (0.32 g, 72%)

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationFiltered off the catalyst
  3. customevaporated to dryness
  4. additionAdded 2M hydrochloric acid
  5. extractionextracted into ethyl acetate
  6. washWashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationFiltered
  9. customevaporated the filtrate
  10. customto give a white solid
  11. customTriturated with diethyl ether

Sources & evidence

ORD record
ord-003ca6c94f63433ba5369c2a85429649
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

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