Tetrahydrofuran → HCID 11065756, compound

HRID 1700496Notes

Reaction equation

HRID 1700496 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=O)[CH2:8]2)=[CH:4][CH:3]=1.Cl.[NH2:16][CH2:17][C:18]#[C:19][CH3:20].O1CCCC1>C(N(CC)CC)C>[Cl:1][C:2]1[S:6][C:5]([CH:7]2[CH2:8][C:9]3[N:16]=[CH:17][CH:18]=[C:19]([CH3:20])[C:10]=3[C:11](=[O:13])[CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12599999But-2-yn-1-amine hydrochlorideHCID 183175185-(5-Chloro-2-thienyl)-1,3-cyclohexanedione

Product 1

HCID 11065756HCID 11065756, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 5-(5-chloro-2-thienyl)cyclohexane-1,3-dione (2.2 g), 1-amino-2-butyne hydrochloride (1.0 g) and tetrahydrofuran (40 ml) was added triethylamine (0.96 g), and the mixture was stirred at room temperature for 1 hour, refluxed for 12 hours and cooled. Insoluble materials were filtered off, and under reduced pressure, the solvent was evaporated. The residue was stirred at 250° C. for 3.5 hours, cooled and purified with silica gel column chromatography (EtOAc/hexane) to give oil of 7-(5-chloro-2-thienyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.79 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 at 250° C. for 3.5 hours
  6. temperaturecooled
  7. custompurified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-026c4710ed174dfbbde5c1f8d53820ad
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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