Pyridine → HCID 11012397, compound

HRID 1700633Notes

Reaction equation

HRID 1700633 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[O:18])[CH2:8]1.N1C=CC=CC=1.S(Cl)([Cl:28])(=O)=O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:6]=[C:5]([Cl:28])[S:4][C:3]=1[CH:7]1[CH2:16][C:15]2[N:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=2[C:9](=[O:18])[CH2:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 18317361HCID 18317361, compound

Product 1

HCID 11012397HCID 11012397, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 7-(3-chlorothiophen-2-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.74 g) in ethyl acetate (10 ml) were added pyridine (0.21 g) and sulfuryl chloride (1.1 g) at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction solution was added ethyl acetate, and the mixture was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) to give 7-(3,5-dichlorothiophen-2-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.56 g).

Workup

  1. washthe mixture was washed with sodium hydrogen carbonate solution, water and saturated brine
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-60fc03fcccc7453a8696347a28dbcc55
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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