Sulfuric Acid → 4,5-Dihydro-6-[4-[[1-(4-pyridinyl)ethylidene]amino]phenyl]-3(2H)-pyridazinone

HRID 1886320Notes

Reaction equation

HRID 1886320 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=2)=[CH:13][CH:12]=1.OS(O)(=O)=O>C1(C)C=CC=CC=1>[N:7]1[CH:8]=[CH:9][C:4]([C:1](=[N:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH2:18][CH2:19][C:20](=[O:23])[NH:21][N:22]=3)=[CH:13][CH:12]=2)[CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 142824-AcetylpyridineHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 138121864,5-Dihydro-6-[4-[[1-(4-pyridinyl)ethylidene]amino]phenyl]-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution containing 0.36 g (0.003 mol) of 4-acetylpyridine and 0.57 g (0.003 mol) of 6-(4-aminophenyl)-4,5-dihydropyridazin-3(2H)one in a mixture of 40 ml of toluene and 40 ml of DMT was refluxed over night with a Dean-Stark separator in the presence of catalytic amount of conc. H2SO4. The solvents were evaporated in vacuo and the residue treated with NaHCO3 -solution. The product was filtered and crystallized from ethanol. Yield 0.53 g (60%).

Workup

  1. customThe solvents were evaporated in vacuo
  2. additionthe residue treated with NaHCO3 -solution
  3. filtrationThe product was filtered
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-610ff4ac75a047df84364effcdaaadb7
Source dataset
uspto-grants-1992_09
Patent number
US05151420

Reaction notes

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