6-(4-amino-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one → 6-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

HRID 1031429Notes

Reaction equation

HRID 1031429 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-])=O>CO.[Pd]>[NH2:16][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 31111876-(4-amino-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 34410526-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 g of 6-(4-amino-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one are dissolved in 2 1 of methanol and hydrogenated over 20 g of 5% palladium-on-charcoal at 20° and 1 bar until absorption ceases. Filtration and evaporation give 6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one, m.p. 195°-196°.

Workup

  1. custom1 bar until absorption ceases
  2. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-7a014fcbbac240ef9286aadd684ca0cc
Source dataset
uspto-grants-1990_09
Patent number
US04954499

Reaction notes

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