Dimethyl Sulfoxide → HCID 13384138, compound

HRID 2287210Notes

Reaction equation

HRID 2287210 reaction equation
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=2)[N:5]=1.[CH3:21][S:22]([CH3:24])=[O:23]>O1CCCC1>[CH3:20][C:16]1[N:15]=[C:14]([C:6]2[N:5]=[C:4]([CH2:21][S:22]([CH3:24])=[O:23])[C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 355191HCID 355191, compound

Product 1

HCID 13384138HCID 13384138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 6 g of sodium hydride (55-60% in paraffin) in 80 ml of anhydrous dimethyl sulphoxide was stirred for 2 hours at 70° C. A solution of 8.8 g of 1-chloro-3-(6-methyl-2-pyridyl)isoquinoline (prepared as described in Example XI) in anhydrous tetrahydrofuran was added dropwise to the mixture with ice-cooling, to obtain a deep red-coloured reaction mixture. The mixture was stirred for 2 hours at 50° C. and was then extracted with dichloromethane, after addition of ice-water. The organic layer was washed with a saturated aqueous sodium chloride solution and with water and the solvent was then distilled off. The residue was dissolved in diethyl ether and ethereal hydrogen chloride was added to the solution. The precipitate obtained was filtered off and dissolved in water. The solution was made alkaline with aqueous sodium hydroxide and extracted with diethyl ether. The ether was distilled off and the residue was crystallised from a mixture of ethanol and pentane. 3-(-6-Methyl-2-pyridyl)-1-methylsulphinylmethylisoquinoline was obtained, melting point 198.0° -198.5° C. A portion of the base was converted into the hydrochloride which, after crystallisation from isopropyl alcohol, melted at 120°-121° C. (decomp.).

Workup

  1. temperaturecooling
  2. customto obtain a deep red-coloured reaction mixture
  3. stirringThe mixture was stirred for 2 hours at 50° C.
  4. extractionwas then extracted with dichloromethane
  5. additionafter addition of ice-water
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution and with water
  7. distillationthe solvent was then distilled off
  8. dissolutionThe residue was dissolved in diethyl ether
  9. additionethereal hydrogen chloride was added to the solution
  10. customThe precipitate obtained
  11. filtrationwas filtered off
  12. dissolutiondissolved in water
  13. extractionextracted with diethyl ether
  14. distillationThe ether was distilled off
  15. customthe residue was crystallised from a mixture of ethanol and pentane

Sources & evidence

ORD record
ord-a7e97f94f91b400cbed73d6d498e64b5
Source dataset
uspto-grants-1981_05
Patent number
US04269834

Reaction notes

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