Water → HCID 86712392, compound

HRID 2174189Notes

Reaction equation

HRID 2174189 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([OH:13])=[CH:7]2.Cl[C:15]1[C:16]([C:21]#[N:22])=[N:17][CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[C:21]([C:16]1[C:15]([O:13][C:8]2[C:9]([CH3:12])=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[CH:20][CH:19]=[CH:18][N:17]=1)#[N:22]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8182583-Chloropyridine-2-carbonitrileHCID 867123931314012-55-9

Product 1

HCID 86712392HCID 86712392, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

4.9 g of 8-fluoro-3-hydroxy-2-methylquinoline, 3.2 g of 3-chloro-2-cyanopyridine and 3.8 g of potassium carbonate were dissolved in 20 ml of N-methylpyrrolidone followed by stirring for 3 hours at 130° C. Subsequently, the reaction solution was cooled to room temperature followed by addition of water and extraction with ethyl acetate. The extract was washed with saturated saline and dried with magnesium sulfate followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 5.37 g of 3-(2-cyano-pyridin-3-yloxy)-8-fluoro-2-methylquinoline.

Workup

  1. temperatureSubsequently, the reaction solution was cooled to room temperature
  2. washThe extract was washed with saturated saline
  3. dry with materialdried with magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4906759ce7914d508e3d5f30f8e91ba6
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

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