4-Aminophenol → HCID 57441055, compound

HRID 1663768Notes

Reaction equation

HRID 1663768 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>[OH-].[Na+]>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][C:2]([O:18][C:15]1[CH:16]=[CH:17][C:12]([NH2:11])=[CH:13][CH:14]=1)=[N:7]2

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-

Product 1

HCID 57441055HCID 57441055, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloroimidazo[1,2-b]pyridazine (768 mg, 5.0 mmol), 4-aminophenol (818 mg, 7.5 mmol), potassium carbonate (2073 mg, 15.0 mmol) and N-methylpyrrolidone (5.0 mL) was stirred at 120° C. for 18 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100) and precipitated from diisopropyl ether to give the title compound (759 mg, 67%) as a gray powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  5. customprecipitated from diisopropyl ether

Sources & evidence

ORD record
ord-a75fe332c9e744d0b8607c397fe27c89
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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