Aluminum(III) Chloride → HCID 66982580, compound

HRID 516256Notes

Reaction equation

HRID 516256 reaction equation
[CH3:1][C:2]([CH3:23])=[CH:3][C:4]([NH:6][C:7]1[CH:22]=[CH:21][C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:23][C:2]1([CH3:1])[C:22]2[C:7](=[CH:8][C:9]3[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11][C:10]=3[CH:21]=2)[NH:6][C:4](=[O:5])[CH2:3]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 66982490HCID 66982490, compound

Product 1

HCID 66982580HCID 66982580, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a solution of 1.032 g of ethyl 7-[(3-methylbut-2-enoyl)amino]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 10.5 ml of dichloromethane was added 870 mg of aluminum chloride at room temperature, followed by stirring at room temperature for 3 hours. Further, 435 mg of aluminum chloride was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into ice-water, followed by extraction with chloroform. The combined organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: Hex-AcOEt) to obtain 431 mg of ethyl 4,4-dimethyl-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a white solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with chloroform
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: Hex-AcOEt)

Sources & evidence

ORD record
ord-7a430556255741d0a85137622e14e272
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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