Dichloromethane → HCID 22493592, compound

HRID 1263460Notes

Reaction equation

HRID 1263460 reaction equation
N1[C:6]([CH3:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].[F:9][C:10]([F:23])([F:22])[S:11]([O:14]S(C(F)(F)F)(=O)=O)(=[O:13])=[O:12].[Cl-].[NH4+:25].[C:26]([O:29][CH2:30]C)(=[O:28])C.CC[CH2:34][CH2:35][CH2:36][CH3:37].Cl[CH2:39]Cl>CN(C)C1C=CN=CC=1>[F:9][C:10]([F:23])([F:22])[S:11]([O:14][C:3]1[C:4]2[C:34](=[C:35]([CH:36]([CH3:37])[CH3:39])[CH:7]=[CH:6][CH:5]=2)[N:25]=[C:8]([C:26]([O:29][CH3:30])=[O:28])[CH:2]=1)(=[O:13])=[O:12]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 21226206Ethyl acetate hexane

Product 1

HCID 22493592HCID 22493592, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In 100 ml of dichloromethane were dissolved 4.2 g of methyl 8-isopropylquinolone-2-carboxylate, 3 ml of 2,6-lutidine and 209 mg of 4-dimethylaminopyridine under a nitrogen gas stream. Trifluoromethanesulfonic anhydride (3.2 ml) was added dropwise to the resulting solution at 0° C., followed by stirring at room temperature for 24 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture and the resulting mixture was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 5% ethyl acetate/n-hexane), whereby 6.3 g of the title compound were obtained in the form of a colorless solid.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washThe organic layer was successively washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue so obtained

Sources & evidence

ORD record
ord-a4e71f244af840219cf2e0809a969fdb
Source dataset
uspto-grants-2003_04
Patent number
US06541474B2

Reaction notes

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