Aluminum(III) Chloride → HCID 67977592, compound

HRID 2174477Notes

Reaction equation

HRID 2174477 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[NH:17][C:18](=[O:27])[CH:19]=[CH:20]C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[C:4]2[C:3]=1[NH:17][C:18](=[O:27])[CH:19]=[CH:20]2

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67976957HCID 67976957, compound

Product 1

HCID 67977592HCID 67977592, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

N-(2-chloro-5-(2-(piperidin-1-yl)ethoxy)phenyl)cinnamamide (436 mg, 1.1 mmol, 1 eq.) was placed in chlorobenzene (2.1 mL), in the presence of aluminium trichloride (906 mg, 1.5 mmol, 6 eq.). The reaction mixture was heated at 125° C. and stirred for 2 hours. After cooling down to room temperature, it was diluted with a water and ice mixture and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-5-(2-(piperidin-1-yl)ethoxy)quinolin-2(1H)-one (225 mg, 67%).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c8388d30859142eca3a4d228d22217d3
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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