Ammonium formate → N-benzyl-3-oxo-6-[4-(hydroxy)phenyl]-2,3-dihydropyridazine-4-carboxamide

HRID 2374774Notes

Reaction equation

HRID 2374774 reaction equation
C([O-])=O.[NH4+].Cl[C:6]1[CH:36]=[C:35](Cl)[CH:34]=[CH:33][C:7]=1[CH2:8][NH:9][C:10]([C:12]1[C:13](=[O:32])[NH:14][N:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)[CH:17]=1)=[O:11]>CO.[OH-].[Pd+2].[OH-]>[CH2:8]([NH:9][C:10]([C:12]1[C:13](=[O:32])[NH:14][N:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH:17]=1)=[O:11])[C:7]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:6]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 9982595N-(2,4-dichlorobenzyl)-3-oxo-6-[4-(benzyloxy)phenyl]-2,3-dihydropyridazine-4-carboxamide

Product 1

HCID 135433902N-benzyl-3-oxo-6-[4-(hydroxy)phenyl]-2,3-dihydropyridazine-4-carboxamideYield 8.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

0.525 g of ammonium formate and 0.022 g of palladium hydroxide were added to 0.4 g of N-(2,4-dichlorobenzyl)-3-oxo-6-[4-(benzyloxy)phenyl]-2,3-dihydropyridazine-4-carboxamide dissolved in 10 cm3 of methanol. The reaction medium was heated and maintained at reflux for 2 hours. After cooling, the reaction medium was suction-filtered through a sinter funnel and the insoluble material was rinsed again with three times 10 cm3 of hot methanol. The organic phase was evaporated under reduced pressure (2 kPa; 45° C.). The residue was recrystallized from methanol. After filtration through a sinter funnel, washing with twice 10 cm3 of methanol and oven-drying under reduced pressure (10 kPa; 50° C.), 0.022 g of N-benzyl-3-oxo-6-[4-(hydroxy)phenyl]-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a yellow solid melting at a temperature above 260° C.

Workup

  1. temperatureThe reaction medium was heated
  2. temperaturemaintained
  3. temperatureat reflux for 2 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction medium was suction-filtered through a sinter funnel
  6. washthe insoluble material was rinsed again with three times 10 cm3 of hot methanol
  7. customThe organic phase was evaporated under reduced pressure (2 kPa; 45° C.)
  8. customThe residue was recrystallized from methanol
  9. filtrationAfter filtration through a sinter funnel
  10. washwashing with twice 10 cm3 of methanol
  11. customoven-drying under reduced pressure (10 kPa; 50° C.)

Sources & evidence

ORD record
ord-17b069e70d1a486ab4beae803326b109
Source dataset
uspto-grants-2008_12
Patent number
US07462613B2

Reaction notes

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