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6-(4-benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one → 5-Methyl-6-(3-amino-4-benzylamino-phenyl)-4,5-dihydro-2H-pyridazine-3-one

HRID 2199061
Notes
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Reaction equation

HRID 2199061 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.[H][H]>C(O)C.C(O)(=O)C.[Pd]>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 117246806-(4-benzylamino-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-oneHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent
HCID 702
Ethanol
Solvent

Procedure

A mixture of 6.75 gm of 5-methyl-6-(3-nitro-4-benzylamino-phenyl)-4,5-dihydro-2H-pyridazine-3-one and 0.7 gm of 10% palladium charcoal in a mixture of 100 ml of ethanol and 20 ml of glacial acetic acid was treated for 3.5 hours at room temperature with hydrogen at 5 bar. The catalyst was filtered off, the filtrate was evaporated, and the residue was used in the next step without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customthe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-e5fe9828c85141868e809d2c863dcb8e
Source dataset
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04361563

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes