5-Amino-8-hydroxyquinoline → 5-Acetyl-2-ethyl-4-[(8-hydroxyquinolin-5-yl)amino]-6-phenylpyridazin-3(2H)-one

HRID 1725539Notes

Reaction equation

HRID 1725539 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].N[C:23]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:23]1[CH:32]=[CH:31][C:30]([OH:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4160025-Amino-8-hydroxyquinolineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 671095445-Acetyl-2-ethyl-4-[(8-hydroxyquinolin-5-yl)amino]-6-phenylpyridazin-3(2H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 80 mg (0.278 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 5-amino-8-quinolinol (67 mg, 0.417 mmol) was added. The resulting mixture was stirred at room temperature during 40 hours and the final product was collected by filtration and washed with diethylether to yield the title compound (100 mg, 90% yield).

Workup

  1. filtrationthe final product was collected by filtration
  2. washwashed with diethylether

Sources & evidence

ORD record
ord-095daebed934457f9f20c568672ff8c2
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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