Ethyl Acetate → HCID 67446904, compound

HRID 42708Notes

Reaction equation

HRID 42708 reaction equation
Cl[C:2]1[C:3](=[O:23])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C([O-])=O.[NH4+].C(OCC)(=O)C>[Pd].CO>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:4]2[C:3](=[O:23])[CH:2]=[C:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[CH:6]=[N:5]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formate2×HCID 674464904-Chloro-2-(4-methoxybenzyl)-5-morpholinopyridazin-3(2H)-one

Product 1

HCID 67446904HCID 67446904, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-chloro-2-(4-methoxybenzyl)-5-(morpholin-4-yl)pyridazin-3(2H)-one (8.56 g, 25.50 mmol) and 10% Pd/C catalyst (1.45 g) in methanol (105 ml) was added ammonium formate (3.70 g, 58.7 mmol), and the mixture was refluxed under argon with TLC monitoring (ethyl acetate). Further portions of ammonium formate were added until the starting material was completely consumed. The catalyst was filtered off and washed with methanol, then the solvent was evaporated under reduced pressure. The residue was taken up in water (30 ml) and extracted with dichloromethane (4×40 ml). The combined extracts were washed with water, dried (Na2SO4) and evaporated. The crude product was purified by crystallization from ethanol (95%).

Workup

  1. customwas completely consumed
  2. filtrationThe catalyst was filtered off
  3. washwashed with methanol
  4. customthe solvent was evaporated under reduced pressure
  5. extractionextracted with dichloromethane (4×40 ml)
  6. washThe combined extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe crude product was purified by crystallization from ethanol (95%)

Sources & evidence

ORD record
ord-70c7a501a0ad4ab782260a29eb67f388
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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