Aluminum(III) Chloride → HCID 69217133, compound

HRID 2415197Notes

Reaction equation

HRID 2415197 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:23])[CH:19]=[C:20]([CH3:22])[CH3:21])[CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:11]1[CH:12]=[C:13]2[C:14]([C:20]([CH3:22])([CH3:21])[CH2:19][C:18](=[O:23])[NH:17]2)=[CH:15][CH:16]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 69217131HCID 69217131, compound

Product 1

HCID 69217133HCID 69217133, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[3-(3-methyl-but-2-enoylamino)-phenyl]-heptanoic acid ethyl ester (3.822 g, 11.5 mmole) in 60 mL of dichloromethane was treated with 4.613 g of aluminum chloride and heated at reflux for four hours. The reaction mixture was poured onto 200 mL of ice-water and extracted with two 100 mL portions of dichloromethane. The combined organic extracts were washed with 200 mL of saturated aqueous sodium bicarbonate solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to yield 3.657 g of 2-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-heptanoic acid ethyl ester as a pale yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for four hours
  3. extractionextracted with two 100 mL portions of dichloromethane
  4. washThe combined organic extracts were washed with 200 mL of saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7885ef4ed6524e5486880261a66eb887
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

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