HCID 19385492, compound → HCID 19385504, compound

HRID 2399358Notes

Reaction equation

HRID 2399358 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=2)=[CH:7][CH:8]=1)N.[H][H]>CO.[Ni]>[NH2:1][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 19385492HCID 19385492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19385504HCID 19385504, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

10 g (36 mmol) of 3-hydrazino-6-[4-methoxy-3-(1-methylethoxy)phenyl]pyridazine are hydrogenated in 100 ml of methanol in the presence of 1 g of Raney nickel with hydrogen under atmospheric pressure at room temperature while stirring efficiently. Starting material is no longer detectable after 4 hours. The solution is filtered to remove catalyst and concentrated in vacuo, and the residue is crystallized from isopropanol/cyclohexane. 4.3 g (46%) of 3-amino-6-[4-methoxy-3-(1-methylethoxy)phenyl]pyridazine of m.p. 184° C. are obtained.

Workup

  1. filtrationThe solution is filtered
  2. customto remove catalyst
  3. concentrationconcentrated in vacuo
  4. customthe residue is crystallized from isopropanol/cyclohexane

Sources & evidence

ORD record
ord-2a9bc8d5480745b89faaf6320146dc8d
Source dataset
uspto-grants-1995_09
Patent number
US05449676

Reaction notes

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