Ethanol → HCID 68485664, compound

HRID 1725546Notes

Reaction equation

HRID 1725546 reaction equation
C(C1C([N+]([O-])=O)=CC(CC)=[C:8]([N:10]2[C:15](=[O:16])[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:9]=1)(=O)C.[NH2:22][C:23]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2.[CH2:34]([OH:36])[CH3:35]>>[C:34]([C:13]1[C:12]([C:23]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:24]=2)=[N:11][N:10]([CH2:8][CH3:9])[C:15](=[O:16])[C:14]=1[NH:22][C:23]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][CH:27]=[N:28]2)(=[O:36])[CH3:35]

Participants

4

Reactant 3

HCID 702EthanolHCID 167704458-Fluoroquinolin-5-amineHCID 68893788HCID 68893788, compound

Product 1

HCID 68485664HCID 68485664, compoundYield 66.7%

Procedure

To a stirred solution of 150 mg (0.522 mmol) of 5-acetyl-2-ethyl-4-nitro-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (8 mL), 5-amino-8-fluoroquinoline (127 mg, 0.783 mmol) (Lee, Jae Keun et al., Bull. Korean Chem. Soc., 1996, 17(1), 90) was added. The resulting mixture was stirred at room temperature for five hours. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 3:1) to yield the title compound (140 mg, 66.7% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-d7b54d03db3843d0926fa4130d931761
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

Loading…