Acetic Acid → 5-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline

HRID 539812Notes

Reaction equation

HRID 539812 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[C:13]([N+:19]([O-])=O)[CH:12]=3)[N:10]=2)[N:7]=1.CC(O)=O>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[C:13]([CH:12]=3)[NH2:19])[N:10]=2)[N:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 575162286-Chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

Product 1

HCID 575162295-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylanilineYield 89.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (4.61 g, 0.0825 mol) is added to a mixture of 6-chloro-2-(4-ethyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (5.0 g, 0.0165 mol) in EtOH—H2O (150 mL, 4:1)containing AcOH (5.66 mL, 0.099 mol) at 80° C. The mixture is stirred at 80° C. for 4 hrs. The reaction mixture is cooled to room temp, filtered through celite, washed with EtOAc and concentrated. The oily residue is dissolved in EtOAc (200 mL) and washed twice with 100 mL Sat. NaHCO3. Compound is concentrated onto celite and purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound (4.02 g, 89%). LCMS m/z=273.3, 275.3 [M+H]+, tR=1.93 min.

Workup

  1. temperatureThe reaction mixture is cooled to room temp
  2. filtrationfiltered through celite
  3. washwashed with EtOAc
  4. concentrationconcentrated
  5. dissolutionThe oily residue is dissolved in EtOAc (200 mL)
  6. washwashed twice with 100 mL Sat. NaHCO3
  7. concentrationCompound is concentrated onto celite
  8. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5d2165add3ab4294976a27be5919c0b0
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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