Methanol → HCID 9842526, compound

HRID 350699Notes

Reaction equation

HRID 350699 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18]4[CH:23]=[N:22][N:21]([CH3:24])[C:20](=[O:25])[C:19]=4Cl)[CH2:11][CH2:10]3)=N[O:8][C:4]=2[CH:3]=1.C[OH:30].[OH-].[Na+]>[Pd].O>[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18]3[CH:23]=[N:22][N:21]([CH3:24])[C:20](=[O:25])[CH:19]=3)[CH2:11][CH2:10]2)=[O:30])=[C:4]([OH:8])[CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 9909267494861-87-9

Product 1

HCID 9842526HCID 9842526, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Into a pressure-tight hydrogenating apparatus 5.0 g (0.0123 mole) of 5-{2-[4-(6-fluoro-1,2-benzisoxazole-3-yl)-piperidine-1-yl]-ethylamino}-4-chloro-2-methyl-2H-pyridazine-3-one, 450 ml of a solvent mixture (a 9:1 mixture of methanol and distilled water), 0.56 g (0.014 mole) of sodium hydroxide and 10 g of a palladium/charcoal catalyst (composition: 8% of palladium, 28% of carbon, 64% of water) are weighed in. The reaction mixture is stirred at room temperature under a hydrogen pressure of 10 atm. for 16 hours. The unreacted hydrogen is removed from the apparatus, the reaction mixture is heated to reflux temperature and stirred at this temperature for 5 minutes. The mixture is filtered hot and the palladium charcoal catalyst is washed three times with 33 ml of a 1:1 mixture of methanol and dichloro methane each. The united mother lyes are evaporated to 15 ml and stirred under cooling with icecold water for half an hour. The precipitated crystals are filtered off. The crude product is recrystallized from 2-propanol. Thus 3.12 g of the desired compound are obtained. Yield 67.8%.

Workup

  1. customThe unreacted hydrogen is removed from the apparatus
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux temperature
  4. stirringstirred at this temperature for 5 minutes
  5. filtrationThe mixture is filtered hot
  6. washthe palladium charcoal catalyst is washed three times
  7. additionwith 33 ml of a 1:1 mixture of methanol and dichloro methane each
  8. customThe united mother lyes are evaporated to 15 ml
  9. stirringstirred
  10. temperatureunder cooling with icecold water for half an hour
  11. filtrationThe precipitated crystals are filtered off
  12. customThe crude product is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-65f13f463aee4f56bfaf226e9a9c3d91
Source dataset
uspto-grants-2007_02
Patent number
US07183283B2

Reaction notes

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