8-Hydroxyquinoline → HCID 59386662, compound

HRID 559606Notes

Reaction equation

HRID 559606 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[CH3:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH:21]=[O:22].C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.C(#N)C.[Cu]I>[CH3:15][C:16]1[N:20]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:4][CH:3]=2)[CH:19]=[N:18][C:17]=1[CH:21]=[O:22]

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 27958875-Methyl-1H-imidazole-4-carbaldehydeHCID 18453089HCID 18453089, compound

Product 1

HCID 59386662HCID 59386662, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

1-(4-Iodophenyl)pyridin-2(1H)-one 6-1 (200 mg, 0.67 mmol) was dissolved in 4 mL DMSO in a sealed tube. To it were added 5-methyl-1H-imidazole-4-carbaldehyde (300 mg, 2.7 mmol), K2CO3 (470 mg, 3.4 mmol), CuI (65 mg, 0.34 mmol) and 8-hydroxyquinoline (50 mg, 0.34 mol). The mixture was stirred at 130° C. for 16 hrs. The mixture was diluted with 100 mL acetonitrile, well stirred, and filtered through a celite layer. The filtrate was concentrated and subjected to prep HPLC to isolate 5-methyl-1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazole-4-carbaldehyde 6-2. MS found for C16H13N3O2 (M+H)+280.1.

Workup

  1. stirringwell stirred
  2. filtrationfiltered through a celite layer
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-02f1467caf2d41c582f02c2dc016bfe1
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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