2-Chloroquinoline → HCID 22241341, compound

HRID 892139Notes

Reaction equation

HRID 892139 reaction equation
COCCOC[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][NH2:12].Cl[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.O>[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[NH:12][CH2:11][C:10]1[CH:9]=[C:8]([OH:7])[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 119282-ChloroquinolineHCID 521998p-Toluenesulfonic acid monohydrateHCID 22241308HCID 22241308, compound

Product 1

HCID 22241341HCID 22241341, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 3-[(2-methoxyethoxy)-methoxy]-benzylamine (422 mg, 2 mmol, example 9) in DMSO (4 mL) is added 2-chloroquinoline (328 mg, 2 mmol). The resulting solution is warmed to 140° C. and stirred at this temperature for 3 h. The resulting mixture is cooled, diluted with water, then extracted with ethyl acetate. The organic extract is washed with brine, dried over MgSO4 and concentrated. The residue is taken up in methanol (10 mL) then p-toluene sulphonic acid monohydrate (190 mg, 1 mmol) is added. This mixture is warmed to 60° C. and stirred at this temperature for 2 h. The reaction mixture is then cooled, concentrated under reduced pressure and the residue purified by flash chromatography (silica, 30% ethyl acetate in dichloromethane) to give the title compound. MS (ESI) 251 (M+H)+.

Workup

  1. temperatureThe resulting mixture is cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. temperatureThis mixture is warmed to 60° C.
  8. stirringstirred at this temperature for 2 h
  9. temperatureThe reaction mixture is then cooled
  10. concentrationconcentrated under reduced pressure
  11. customthe residue purified by flash chromatography (silica, 30% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-e2d3c002c186472da4e4db2d7ef98bf9
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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