Tetrahydrofuran → HCID 10945005, compound

HRID 1700480Notes

Reaction equation

HRID 1700480 reaction equation
[F: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>[F: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 136448415-(2-Fluorophenyl)cyclohexane-1,3-dione

Product 1

HCID 10945005HCID 10945005, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-(2-fluorophenyl)cyclohexane-1,3-dione (0.98 g), 1-amino-2-butyne hydrochloride (0.5 g), molecular sieves 4A (2 g) and tetrahydrofuran (20 ml) was added triethylamine (0.48 g), and the mixture was stirred at room temperature for 1 hour, refluxed for 12 hours and cooled. Insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was stirred for 6 hours at 220° C. and cooled, 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) to give oil of 7-(2-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.35 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 6 hours at 220° C.
  6. temperaturecooled, to which
  7. additionwere 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-776b45d049b64115b3ab1ef28c33c1f8
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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