Tetrahydrofuran → 7-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 49183Notes

Reaction equation

HRID 49183 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]1.Cl.[NH2:17][CH2:18][C:19]#[C:20][CH3:21].O1CCCC1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][C:10]2[N:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:11]=2[C:12](=[O:14])[CH2:13]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8753605-(2-Chlorophenyl)cyclohexane-1,3-dioneHCID 12599999But-2-yn-1-amine hydrochloride

Product 1

HCID 110655617-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneYield 15.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5-(2-chlorophenyl)-1,3-cyclohexanedione (1.1 g), 1-amino-2-butyne hydrochloride (0.5 g), molecular sieve 4A (2 g) and tetrahydrofuran (20 ml) was combined with triethylamine (0.48 g), stirred at room temperature for 1 hour, and then heated under reflux for 12 hours. After cooling, insolubles were filtered off, and the solvent was distilled off under reduced pressure. The residue was stirred at 220° C. for 4 hours. Ethyl acetate and aqueous sodium hydrogen carbonate were added, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was subjected to a column chromatography on a silica gel (EtOAc/hexane) to obtain a crystal which was then recrystallized from ethyl acetate-hexane to obtain 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinoline-5-one (0.20 g) as a colorless crystal.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. filtrationinsolubles were filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. stirringThe residue was stirred at 220° C. for 4 hours
  7. additionEthyl acetate and aqueous sodium hydrogen carbonate were added
  8. washthe organic layer was washed successively with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationAfter concentrating under reduced pressure
  11. customto obtain a crystal which
  12. customwas then recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f0cb37404f784b81bf0d9f675b89ee0d
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

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