8-Hydroxyquinoline → HCID 22181534, compound

HRID 2217580Notes

Reaction equation

HRID 2217580 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[N:10]1[NH:11][C:12](=[O:16])[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.[Cu]I>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([N:11]2[C:12](=[O:16])[CH:13]=[CH:14][CH:15]=[N:10]2)=[CH:8][C:2]=1[F:1]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 681533(2H)-PyridazinoneHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 22181534HCID 22181534, compound

Reagents, catalysts & solvents 2

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

Procedure

2-Fluoro-4-iodoaniline (0.5 g, 2.10 mmol) was combined with 2H-Pyridazin-3-one (0.243 g, 2.53 mmol), CuI (0.06 g, 0.315 mmol), K2CO3 (0.32 g, 2.31 mmol), and 8-hydroxyquinoline (0.046 g, 0.315 mmol) in DMSO (3 mL). The mixture was degassed with a stream of argon and then heated at reflux for 23 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 (0.16 g, 37%) as a yellow solid. MS: APCI (AP+): 206.1 (M)+.

Workup

  1. customThe mixture was degassed with a stream of argon
  2. temperatureheated
  3. temperatureat reflux for 23 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 (0.16 g, 37%) as a yellow solid

Sources & evidence

ORD record
ord-829182c5336047c2a2a5375af885d3dd
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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