8-Hydroxyquinoline → 1-(4-Amino-3-fluorophenyl)pyridin-2-one

HRID 559590Notes

Reaction equation

HRID 559590 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[OH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.C(O)CCC.O>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[O:10])=[CH:8][C:2]=1[F:1]

Participants

9

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 1856942-Fluoro-4-iodoanilineHCID 178516071HCID 178516071, compound

Product 1

HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-oneYield 89.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-fluoro-4-iodoaniline (3.00 g, 12.6 mmol), 2-hydroxypyridine 1-7 (1.20 g, 12.6 mmol), 8-hydroxyquinoline (0.184 g, 1.26 mmol) and K2CO3 (3.49 g, 25.3 mmol) in DMSO (20 mL) was degassed with Ar before being charged with CuI (0.241 g, 1.27 mmol). The mixture in a sealed tube was heated at 130° C. overnight. After being cooled down to room temperature, H2O and nBuOH were added. The organic phase was separated, concentrated in vacuo to give 1-(4-amino-3-fluorophenyl)pyridin-2(1H)-one as a solid (2.31 g).

Workup

  1. customwas degassed with Ar
  2. temperatureAfter being cooled down to room temperature
  3. customThe organic phase was separated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca5aef8f78084bebaa961d26b7f5f781
Source dataset
uspto-grants-2011_11
Patent number
US08063077B2

Reaction notes

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