6-(4'-Amino-3'-nitro-phenyl)-4,5-dihydro-3(2H)-pyridazinone → 6-(3',4'-Diamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 2398937Notes

Reaction equation

HRID 2398937 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:15]([O-])=O>C(O)C.[Pt](=O)=O>[NH2:15][C:3]1[CH:4]=[C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 221678336-(4'-Amino-3'-nitro-phenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 200815866-(3',4'-Diamino-phenyl)-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

4.68 gm of 6-(4'-amino-3'-nitro-phenyl)-4,5-dihydro-3(2H)-pyridazinone werehydrogenated in 500 ml of ethanol at 40° C. for 4 hours in the presence of 1 gm of platinum dioxide at 5 atmospheres. Thereafter, the solution was cooled and filtered, and the filter cake was boiled with a mixture of 4 parts of isopropanol and 1 part of water. The resulting mixture was filtered, and upon cooling, the desired product crystallized out of the filtrate; m.p. 226° C.

Workup

  1. temperatureThereafter, the solution was cooled
  2. filtrationfiltered
  3. additionthe filter cake was boiled with a mixture of 4 parts of isopropanol and 1 part of water
  4. filtrationThe resulting mixture was filtered
  5. temperatureupon cooling
  6. customthe desired product crystallized out of the filtrate

Sources & evidence

ORD record
ord-88cf3cfcd6884048bcb8f2bf35f0c0e5
Source dataset
uspto-grants-1977_05
Patent number
US04026891

Reaction notes

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