Aluminum(III) Chloride → HCID 67976269, compound

HRID 2174466Notes

Reaction equation

HRID 2174466 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][O: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][O: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 67974987HCID 67974987, compound

Product 1

HCID 67976269HCID 67976269, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

N-(2-chloro-5-(2-morpholinoethoxy)phenyl)cinnamamide (800 mg, 2.1 mmol, 1 eq.) was placed in chlorobenzene (1.9 mL), in the presence of aluminium trichloride (1.6 g, 12.4 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-morpholinoethoxy)quinolin-2(1H)-one (220 mg, 34%).

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-ba189f3d946242fda2b62536c6d0da93
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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