8-Hydroxyquinoline → 1-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde

HRID 559605Notes

Reaction equation

HRID 559605 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[NH:11][CH:12]=[C:13]([CH:15]=[O:16])[N:14]=1.C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.O1CCOCC1.[Cu]I.O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH:12]=[C:13]([CH:15]=[O:16])[N:14]=[C:10]2[CH3:9])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 12208p-DiiodobenzeneHCID 178418999HCID 178418999, compound

Product 1

HCID 593866581-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 1,4-diiodobenzene 1-1 (600 mg, 1.8 mmol), 2-methyl-1H-imidazole-4-carbaldehyde (200 mg, 1.8 mmol), K2CO3 (503 mg, 3.6 mmol), CuI (105 mg, 0.55 mmol) and 8-hydroxyquinoline (80 mg, 0.55 mol) in 5 mL DMSO and 5 mL dioxane in a sealed tube was stirred for 2 days at 120° C. It was cooled to rt, and to it was added 60 mL water. The mixture was stirred for 30 min and filtered through a celite layer. The filtrate was concentrated in vacuo and subjected to reverse phase preparative HPLC to isolate 1-(4-iodophenyl)-2-methyl-1H-imidazole-4-carbaldehyde 5-1. MS found for C11H9IN2O (M+H)+313.0.

Workup

  1. temperatureIt was cooled to rt
  2. stirringThe mixture was stirred for 30 min
  3. filtrationfiltered through a celite layer
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d97fc436d21c4e01a965fa5471e02b08
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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