Hydrochloric Acid → HCID 86712394, compound

HRID 2174190Notes

Reaction equation

HRID 2174190 reaction equation
C([C:3]1[C:8]([O:9][C:10]2[C:11]([CH3:21])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])=[CH:7][CH:6]=[CH:5][N:4]=1)#N.[CH3:22][Mg]Cl.Cl.[C:26](=[O:29])(O)[O-].[Na+]>O1CCCC1>[CH3:21][C:11]1[C:10]([O:9][C:8]2[C:3]([C:26](=[O:29])[CH3:22])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:19][C:18]2[C:13](=[C:14]([F:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86712392HCID 86712392, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86712394HCID 86712394, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.51 g of 3-(2-cyano-pyridin-3-yloxy)-8-fluoro-2-methylquinoline were dissolved in 30 ml of dehydrated tetrahydrofuran. 3.6 ml of a 3 M tetrahydrofuran solution of methylmagnesium chloride were dropped therein while cooling with ice followed by stirring the reaction solution for 2 hours while continuing to cool with ice. Subsequently, the reaction solution was added to 1 N hydrochloric acid solution followed by neutralizing with aqueous sodium bicarbonate and then extracting 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 1.7 g of 1-[3-(2-methyl-8-fluoroquinolin-3-yloxy)-pyridin-2-yl]-ethanone.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureto cool with ice
  3. extractionextracting with ethyl acetate
  4. washThe extract was washed with saturated saline
  5. dry with materialdried with magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cd9dc4e623c84c8aafcd5ee322a52cca
Source dataset
uspto-grants-2015_06
Patent number
US09060517B2

Reaction notes

Loading…