Aluminum(III) Chloride → HCID 69217133, compound

HRID 899285Notes

Reaction equation

HRID 899285 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-1966c6c6342f4e6e8c672737d87b95ea
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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