6-[4-(2-methyl-2-nitropropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone → 6-[4-(2-amino-2-methylpropyl amino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1905420Notes

Reaction equation

HRID 1905420 reaction equation
[CH3:1][C:2]([N+:20]([O-])=O)([CH3:19])[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][CH:6]=1>[Ni].CN(C)C=O>[NH2:20][C:2]([CH3:1])([CH3:19])[CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]([CH3:18])[CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 104947216-[4-(2-methyl-2-nitropropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 106123876-[4-(2-amino-2-methylpropyl amino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 91.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-[4-(2-methyl-2-nitropropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (412.6 g), Raney nickel (100 ml) and dimethylformamide (1.5 liters) was hydrogenated under atmospheric pressure. After the absorption of hydrogen ceased, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was recrystallized from methanol to give 6-[4-(2-amino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (340.39 g).

Workup

  1. customAfter the absorption of hydrogen
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-e65ac7272fcb428bbd8c01b7bdc85926
Source dataset
uspto-grants-1989_06
Patent number
US04843072

Reaction notes

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