Chloroacetone → 7-Iodo-2-methyl-imidazo[1,2-a]quinoline

HRID 2075659Notes

Reaction equation

HRID 2075659 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[CH:6]=[CH:5]2.Cl[CH2:14][C:15](=O)[CH3:16].C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:14]=[C:15]([CH3:16])[N:12]=[C:7]1[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 589078666-Iodoquinolin-2-amine

Product 1

HCID 670913497-Iodo-2-methyl-imidazo[1,2-a]quinoline

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Iodo-quinolin-2-ylamine (270 mg, 1.0 mmol), chloroacetone (111 mg, 1.2 mmol), sodium bicarbonate (252 mg, 3.0 mmol), and catalytic tetrabutylammonium iodide were dissolved in 1,4-dioxane and water, and stirred at 80° C. overnight. The reaction was cooled to room temperature and concentrated, and the residue was purified by preparative HPLC to give the desired compound, 1m.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b8743c82f76c40b78afa318037795788
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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