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6-Chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine → 5-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-aniline

HRID 539788
Notes
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Reaction equation

HRID 539788 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+:18]([O-])=O)[CH:12]=3)=[CH:10][N:4]2[N:3]=1>[Fe].CCO.CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([CH:12]=3)[NH2:18])=[CH:10][N:4]2[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

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

Product 1

HCID 866678585-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-anilineYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (1.34 g) is added to a mixture of 6-chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine (1.15 g, 0.004 mol) and EtOH—AcOH (120 mL, 2:1). The mixture is stirred at 80° C. for 2 hours, cooled to room temperature, filtered through celite which is washed with EtOAc, and concentrated. The oily residue is dissolved in EtOAc (500 mL) and washed once with sat. NaHCO3 (200 mL). Organic layer is dried and concentrated to give the title compound (0.85 g, 82%), which is used without further purification. LCMS m/z=259.4 [M+H]+, tR=1.64 min.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through celite which
  3. washis washed with EtOAc
  4. concentrationconcentrated
  5. dissolutionThe oily residue is dissolved in EtOAc (500 mL)
  6. washwashed once with sat. NaHCO3 (200 mL)
  7. customOrganic layer is dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7dc52769f8364ff281676b74645f9476
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871767B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes