8-Hydroxyquinoline → HCID 22181502, compound

HRID 2217470Notes

Reaction equation

HRID 2217470 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[NH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=[O:15].C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.[Cu]I>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[O:15])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 885792-Pyridinamine, 5-iodo-

Product 1

HCID 22181502HCID 22181502, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

2-Amino-5-iodopyridine (5.0 g, 22.7 mmol) was combined with 1H-pyridin-2-one (2.59 g, 27.27 mmol), CuI (0.65 g, 3.41 mmol), K2CO3 (3.45 g, 24.9 mmol), and 8-hydroxyquinoline (0.49 g, 3.40 mmol) in DMSO (20 mL). The mixture was degassed with a stream of argon and then heated at reflux for 18 h before cooling to RT. 10% aq. NH4OH and EtOAc were added, and the mixture was filtered through a plug of layered celite and decolorizing charcoal, eluting with EtOAc. The filtrate was concentrated under reduced pressure. Purification of the crude product by mplc revealed A (0.40 g, 10%) as a yellow solid. MS: APCI (AP+): 188.1 (M)+.

Workup

  1. customThe mixture was degassed with a stream of argon
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. addition10% aq. NH4OH and EtOAc were added
  5. filtrationthe mixture was filtered through a plug of layered celite
  6. washeluting with EtOAc
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customPurification of the crude product by mplc revealed A (0.40 g, 10%) as a yellow solid

Sources & evidence

ORD record
ord-519d2f9d40ec421a9b442096ec025c75
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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