8-Aminoquinoline → HCID 68485702, compound

HRID 1725523Notes

Reaction equation

HRID 1725523 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:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH: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:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 68485702HCID 68485702, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 100 mg (0.348 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (pal Piaz, V et al., J. Med. Chem. 1997, 40, 1417) in 5 ml of ethanol, 75 mg (0.522 mmol) of 8-aminoquinoline was added. The resulting mixture was stirred at room temperature for two hours and the final product was collected by filtration and washed with diethylether to yield the title compound (100 mg, 74.6% yield).

Workup

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

Sources & evidence

ORD record
ord-ebfcc4a2070741b8991e1bb1a3395c2b
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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