Aluminum(III) Chloride → HCID 67200304, compound

HRID 547282Notes

Reaction equation

HRID 547282 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:13]([CH3:16])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[O:5]=[C:4]1[CH2:3][CH2:2][C:12]2[C:7](=[CH:8][C:9]([CH:13]([CH3:16])[C:14]#[N:15])=[CH:10][CH:11]=2)[NH:6]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67200973HCID 67200973, compound

Product 1

HCID 67200304HCID 67200304, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[3-(3-chloropropionylamino)phenyl]propionitrile (0.654 g, 2.77 mmol) in CH2Cl2 (8 mL) at 0° C. AlCl3, (1.10 g, 8.31 mmol) was added portionwise. The reaction mixture was stirred 5 min, then was refluxed 8 h. After cooling at 0° C., the mixture was washed with 6N HCl solution (3×10 mL), water (3×10 mL) and brine (2×10 mL). After drying over Na2SO4 and solvent evaporation a crude residue was obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 85:15), afforded 2-(2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl]propionitrile as yellow oil (0.345 g, 1.72 mmol). Yield 62%.

Workup

  1. customat 0° C
  2. temperaturewas refluxed 8 h
  3. washthe mixture was washed with 6N HCl solution (3×10 mL), water (3×10 mL) and brine (2×10 mL)
  4. dry with materialAfter drying over Na2SO4 and solvent evaporation a crude residue
  5. customwas obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 85:15)

Sources & evidence

ORD record
ord-8154f2d47be34e03bc676297390b270e
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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