Hydrazine hydrate (1:1) → 5-Methyl-6-(3-amino-4-benzylamino-phenyl)-4,5-dihydro-2H-pyridazine-3-one

HRID 2290240Notes

Reaction equation

HRID 2290240 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([N+:22]([O-])=O)[CH:9]=2)=[N:6][NH:5][C:4](=[O:25])[CH2:3]1.O.NN>[Ni].C(O)C>[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([NH2:22])[CH:9]=2)=[N:6][NH:5][C:4](=[O:25])[CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 117246806-(4-benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 131366765-Methyl-6-(3-amino-4-benzylamino-phenyl)-4,5-dihydro-2H-pyridazine-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

12.5 gm (36.9 mmols) of 5-methyl-6-[3'-nitro-4'-benzylamino-phenyl]-4,5-dihydro-3(2H)-pyridazinone were added to a mixture of 20 ml of 99% hydrazine hydrate and 350 ml of ethanol, and then 10 gm of Raney nickel were added. After 24 hours' stirring at room temperature, the solid components were suction-filtered off, dissolved in dimethyl formamide, the catalyst was filtered off, and the filtrate was evaporated. The crystalline residue thus obtained was digested with ethanol, washed with ether and dried.

Workup

  1. filtrationthe solid components were suction-filtered off
  2. dissolutiondissolved in dimethyl formamide
  3. filtrationthe catalyst was filtered off
  4. customthe filtrate was evaporated
  5. customThe crystalline residue thus obtained
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-b795b5913d484ea7b483943c5a037b01
Source dataset
uspto-grants-1986_10
Patent number
US04616018

Reaction notes

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