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 2199065Notes

Reaction equation

HRID 2199065 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]>CN(C)C=O.[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 6228DimethylformamideSolvent

Procedure

203 gm of 5-methyl-6-[3-nitro-4-(4-methoxy-benzoylamino)-phenyl]-4,5-dihydro-2H-pyridazine-3-one were dissolved in 1.7 liters of dimethylformamide, and the solution was treated with hydrogen in the presence of 20 gm of 10% palladium charcoal for 2 hours at a pressure of 5 bar. After filtering off the catalyst, the filtrate was poured into 7.5 liters of ice water. The precipitated product was dried at 120° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. additionthe filtrate was poured into 7.5 liters of ice water
  3. customThe precipitated product was dried at 120° C.

Sources & evidence

ORD record
ord-9945fd92700848e9a104aad370a30ddb
Source dataset
uspto-grants-1982_11
Patent number
US04361563

Reaction notes

Loading…