8-Hydroxyquinoline → HCID 18453089, compound

HRID 1802621Notes

Reaction equation

HRID 1802621 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 36.2%

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 (4.00 g, 12.1 mmol), 2-hydroxypyridine 1-7 (1.15 g, 12.1 mmol), 8-hydroxyquinoline (176 mg, 1.21 mmol) and K2CO3 (1.74 g, 12.6 mmol) in DMSO (16 mL) was degassed with Ar before being charged with CuI (230 mg, 1.21 mmol). The mixture in a sealed tube was heated at 130° C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with EtOAc in hexanes (0-70% EtOAc) to give 1-(4-iodophenyl)pyridin-2(1H)-one (1.30 g).

Workup

  1. customwas degassed with Ar
  2. temperatureAfter being cooled to room temperature
  3. filtrationIt was filtered through celite
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column
  8. washeluted with EtOAc in hexanes (0-70% EtOAc)

Sources & evidence

ORD record
ord-b287a01d452b4558b15ac954f23d98c1
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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