6-Amino-3-chloropyridazine → 6-Chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine

HRID 539787

Reaction equation

HRID 539787 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1)=O>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2=[N:8][C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)=[CH:10][N:6]2[N:7]=1

Participants

5

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 38004222-Bromo-1-(4-methyl-3-nitrophenyl)ethan-1-one

Product 1

HCID 866678576-Chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazineYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 6-chloropyridazin-3-amine (18.4 g, 0.14 mol) and 2-bromo-1-(4-methyl-3-nitro-phenyl)ethanone (36.13 g, 0.14 mol) in acetonitrile (219 mL) is heated at reflux for 18 hr. The mixture is diluted with water (500 mL), stirred at room temperature for 1 hour and solids are collected by filtration to give the title compound (35.65 g, 88% yield). LCMS m/z=289.4 [M+H]+, tR=2.65 min.

Workup

  1. temperatureat reflux for 18 hr
  2. filtrationsolids are collected by filtration

Sources & evidence

ORD record
ord-c6d8e6a97087478db212b0bdbb34b055
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Linked notes

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