Tetrahydrofuran → 4-Methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700478

Reaction equation

HRID 1700478 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]1.Cl.[NH2:17][CH2:18][C:19]#[C:20][CH3:21].O1CCCC1>C(N(CC)CC)C>[CH3:21][C:20]1[C:11]2[C:10](=[O:15])[CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[CH2:13][C:12]=2[N:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12599999But-2-yn-1-amine hydrochlorideHCID 17606575HCID 17606575, compound

Product 1

HCID 109339624-Methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-oneYield 27.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-(2-methylphenyl)cyclohexane-1,3-dione (1.5 g), 1-amino-2-butyne hydrochloride (0.86 g), molecular sieves 4A (2 g) and tetrahydrofuran (20 ml) was added triethylamine (0.74 g), and the mixture was stirred at room temperature for 1 hour and then refluxed for 17 hours and cooled. Insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was stirred at 220° C. for 4 hours, to which were added ethyl acetate and sodium hydrogen carbonate solution. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane). The resulting crystals were recrystallized from ethyl acetate-hexane to give colorless crystals of 4-methyl-7-(2-methylphenyl)-5,6,7,8-tetrahydroquinolin-5-one (0.52 g).

Workup

  1. temperaturerefluxed for 17 hours
  2. temperaturecooled
  3. filtrationInsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. stirringthe residue was stirred at 220° C. for 4 hours, to which
  6. additionwere added ethyl acetate and sodium hydrogen carbonate solution
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  11. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f83281d605a8455db1e59cf654f4f318
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Linked notes

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