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 930553Notes

Reaction equation

HRID 930553 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][C:10]=1[N+:23]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C1COCC1.[Ni]>[NH2:23][C:10]1[CH:11]=[C:12]([C:15]2[CH:16]([CH3:22])[CH2:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:13]=[CH:14][C:9]=1[NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

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 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Benzylamino-3-nitro-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one E-4.1′ (662 mg; 1.96 mmol) is solved in 200 ml THF, a scoop of Raney Nickel is then added. The mixture is placed in the hydrogenation apparatus and stirred at RT for 1.5 hours under 4 bar hydrogen pressure. The Raney Nickel is filtered off and the reaction solution evaporated to dryness.

Workup

  1. filtrationThe Raney Nickel is filtered off
  2. customthe reaction solution evaporated to dryness

Sources & evidence

ORD record
ord-a355178025084474a8cf84c2d6d9af0e
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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