Aluminum(III) Chloride → HCID 67977265, compound

HRID 2174472Notes

Reaction equation

HRID 2174472 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:28])/[C:19](/[CH3:27])=[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:28])[C:19]([CH3:20])=[CH:27]2

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67974754HCID 67974754, compound

Product 1

HCID 67977265HCID 67977265, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

(E)-N-(2-chloro-5-(2-(piperidin-1-yl)ethoxy)phenyl)-2-methyl-3-phenylacrylamide (100 mg, 0.2 mmol, 1 eq.) was placed in chlorobenzene (500 μL), in the presence of aluminium trichloride (201 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-3-methyl-5-(2-(piperidin-1-yl)ethoxy)quinolin-2(1H)-one (25 mg, 31%).

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-7e8845ca6692476bb8cb247866728f07
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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