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

HRID 1700489Notes

Reaction equation

HRID 1700489 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=O)[CH2:10]1.Cl.[NH2:18][CH2:19][C:20]#[C:21][CH3:22].O1CCCC1>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:10][C:11]2[N:18]=[CH:19][CH:20]=[C:21]([CH3:22])[C:12]=2[C:13](=[O:15])[CH2:14]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12599999But-2-yn-1-amine hydrochlorideHCID 171223135-(2-Methoxyphenyl)-1,3-cyclohexanedione

Product 1

HCID 111190487-(2-Methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneYield 32.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-(2-methoxyphenyl)-1,3-cyclohexanedione (1.0 g), 1-amino-2-butyne hydrochloride (0.5 g), molecular sieves 4A (2 g) and tetrahydrofuran (20 ml) was added triethylamine (0.48 g). The mixture was stirred at room temperature for 1 hour, refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was stirred for 4 hours at 220° C. and cooled, to which was 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) to give oil of 7-(2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.4 g).

Workup

  1. temperaturerefluxed for 12 hours
  2. temperaturecooled
  3. filtrationinsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. stirringthe residue was stirred for 4 hours at 220° C.
  6. temperaturecooled, to which
  7. additionwas added ethyl acetate and sodium hydrogen carbonate solution
  8. washThe organic layer was washed with water and saturated brine
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-9bdc0805bffe462dbbb2090bbdcc4f4b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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