4-Methoxy-N-[2-nitro-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]benzamide → N-[2-Amino-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]-4-methoxy-benzamide

HRID 2199056Notes

Reaction equation

HRID 2199056 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:10]([N+:25]([O-])=O)[CH:9]=2)=[N:6][NH:5][C:4](=[O:28])[CH2:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:10]([NH2:25])[CH:9]=2)=[N:6][NH:5][C:4](=[O:28])[CH2:3]1

Participants

5

Reactant 2

HCID 138508804-Methoxy-N-[2-nitro-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 13850881N-[2-Amino-4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]-4-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9.8 gm of 5-methyl-6-[3-nitro-4-(4-methoxy-benzoylamino)-phenyl]-3-oxo-4,5-dihydro-2H-pyridazine were dissolved in 1000 ml of ethanol and hydrogenated for 24 hours at room temperature with a hydrogen pressure of 5 bar in the presence of 1 gm of 10% palladium charcoal. The obtained precipitate was suction filtered and used in the next step without removing the catalyst. A further fraction of the product can be obtained from the mother liquors.

Workup

  1. filtrationfiltered
  2. customwithout removing the catalyst
  3. customA further fraction of the product can be obtained from the mother liquors

Sources & evidence

ORD record
ord-16957286d7e142388c4251bff0d3b389
Source dataset
uspto-grants-1982_11
Patent number
US04361563

Reaction notes

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