Water → HCID 59370524, compound

HRID 2046690Notes

Reaction equation

HRID 2046690 reaction equation
[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[C:18](F)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[Li+].[Li+].O>CS(C)=O>[Cl:11][C:12]1[CH:19]=[C:18]([N:1]2[CH:10]3[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]3)[CH2:4][CH2:3][CH2:2]2)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 6994355QUINOLINE, DECAHYDRO-, CIS-

Product 1

HCID 59370524HCID 59370524, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution (2 mL) of cis-decahydroquinoline (447 mg), 2-chloro-4-fluorobenzonitrile (500 mg) and lithium carbonate (237 mg) in dimethyl sulfoxide was reacted at 140° C. for 10 min in a microwave reaction apparatus. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→1:1) to give the title compound as a colorless oil (yield: 600 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-af03df7b9c7d4b0c8c00dc4c05704a1c
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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