Diethyl Ether → HCID 22247291, compound

HRID 1531987Notes

Reaction equation

HRID 1531987 reaction equation
[Al].[Li].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:8][C:9]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=O)[NH:14]2.[CH3:21][CH2:22][O:23]CC>>[C:22]([N:14]1[C:15]2[C:10](=[C:9]([CH3:8])[CH:18]=[C:17]([CH3:19])[CH:16]=2)[CH2:11][CH2:12][CH2:13]1)(=[O:23])[CH3:21]

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 166653HydrideHCID 6451240Aluminum(III) ChlorideHCID 16211445Aluminum;lithiumHCID 22247325154205-24-0

Product 1

HCID 22247291HCID 22247291, compound

Procedure

Lithium aluminum. hydride (687 mg) was suspended in ether (16 ml), and aluminum chloride (4.2 g) was added. A solution of 5,7-dimethylquinolone (1.6 g) in ether (16 ml) was dropwise added and the mixture was refluxed for 0.5 hr. The reaction mixture was poured into ice water (100 ml) and extracted with chloroform (100 ml). After washing with water, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained 5,7dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in chloroform (30 ml), and acetic anhydride (929 mg) was added, which was followed by stirring at room temperature for 1 hr. Chloroform (100 ml) was added to the reaction mixture, and the mixture was washed successively with saturated aqueous solution of sodium hydrogencarbonate and water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzene=1/5−1/1) to give 1.5 g of oily 1-acetyl-5,7-dimethyl-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperaturethe mixture was refluxed for 0.5 hr
  2. extractionextracted with chloroform (100 ml)
  3. washAfter washing with water
  4. dry with materialthe chloroform layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionThe obtained 5,7dimethyl-1,2,3,4-tetrahydroquinoline was dissolved in chloroform (30 ml)
  7. additionacetic anhydride (929 mg) was added
  8. additionChloroform (100 ml) was added to the reaction mixture
  9. washthe mixture was washed successively with saturated aqueous solution of sodium hydrogencarbonate and water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/benzene=1/5−1/1)

Sources & evidence

ORD record
ord-b8f2b03ec1834654936234c47ce6ebe9
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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