Tetrahydrofuran → HCID 11099106, compound

HRID 1700488Notes

Reaction equation

HRID 1700488 reaction equation
[Br: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>[Br: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 12599999But-2-yn-1-amine hydrochlorideHCID 18317391HCID 18317391, compound

Product 1

HCID 11099106HCID 11099106, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-(2-bromophenyl)cyclohexane-1,3-dione (1.5 g), 1-amino-2-butyne hydrochloride (0.59 g) and tetrahydrofuran (30 ml) was added triethylamine (0.57 g). The mixture was stirred at room temperature for 1 hour, refluxed for 13 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and to the residue was added diphenylether. The mixture was stirred at 250° C. for 12 hours and cooled, and to the mixture was added diethylether. The mixture was extracted with 1N hydrochloric acid, and the aqueous layer was washed with diethylether, neutralized with 1N sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give crystals of 7-(2-bromophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.52 g).

Workup

  1. temperaturerefluxed for 13 hours
  2. temperaturecooled
  3. filtrationinsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. additionto the residue was added diphenylether
  6. stirringThe mixture was stirred at 250° C. for 12 hours
  7. temperaturecooled
  8. additionto the mixture was added diethylether
  9. extractionThe mixture was extracted with 1N hydrochloric acid
  10. washthe aqueous layer was washed with diethylether
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried with magnesium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40c647fe534c45f49eff8e122ea7496c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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