8-Hydroxyquinoline → HCID 18453089, compound

HRID 1802602Notes

Reaction equation

HRID 1802602 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[I:8][C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[O:9])=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 12208p-DiiodobenzeneHCID 178516071HCID 178516071, compound

Product 1

HCID 18453089HCID 18453089, compoundYield 42.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1,4-diiodobenzene 1-1 (2.00 g, 6.06 mmol), 2-hydroxypyridine 1-7 (0.576 g, 6.06 mmol), 8-hydroxyquinoline (0.088 g, 0.61 mmol) and K2CO3 (0.870 g, 6.30 mmol) in DMSO (8 mL) was degassed with Ar before being charged with CuI (0.115 g, 0.61 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered through CELITE. The organic layer was separated, then applied to a silica gel column, which was eluted with 0-70% EtOAc in hexane to give 1-(4-iodophenyl)pyridin-2(1H)-one as a solid (0.760 g). MS 298.0 (M+H).

Workup

  1. customwas degassed with Ar
  2. filtrationThe mixture was filtered through CELITE
  3. customThe organic layer was separated
  4. washwas eluted with 0-70% EtOAc in hexane

Sources & evidence

ORD record
ord-8a75e05c1502494b900c5f9121c160df
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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