HCID 14459483, compound → HCID 14459488, compound

HRID 1031468Notes

Reaction equation

HRID 1031468 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]([CH3:18])[CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[N+:19]([O-])=O.[H][H]>CO.[Pd]>[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]([CH3:18])[CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][C:6]=1[NH2:19]

Participants

5

Reactant 2

HCID 14459483HCID 14459483, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14459488HCID 14459488, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.0 g (10.3 mmol) of 6-[4-(2-aminoethyl)amino-3-nitro-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone in 200 ml of methanol are hydrogenated under a hydrogen pressure of 2 bar at room temperature in the presence of 0.5 g of palladium charcoal (10% Pd) until uptake of hydrogen ceases. After removal of the catalyst by filtration, the solution is concentrated by evaporation under vacuum. The residue is chromatographed on silica gel with methanol/conc. ammonia (95/5) as solvent. The main fraction is concentrated by evaporation under vacuum and the solid obtained is recrystallized from ethanol. 1.37 g (51%) of a beige coloured solid, m.p. 176°-177° C. are obtained.

Workup

  1. customat room temperature
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. concentrationthe solution is concentrated by evaporation under vacuum
  5. customThe residue is chromatographed on silica gel with methanol/conc
  6. concentrationThe main fraction is concentrated by evaporation under vacuum
  7. customthe solid obtained
  8. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-169c741266fc435ab655b58dfe0530ab
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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