Methanol → 2-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate

HRID 1649416Notes

Reaction equation

HRID 1649416 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.CO.[OH-].[K+].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>CN(C)C=O>[CH3:17][S:18]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chloride2×HCID 1691533,4-Dihydro-5-hydroxy-2(1H)-quinolinone

Product 1

HCID 128996762-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonateYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g of 5-hydroxy-3,4-dihydrocarbostyril was added to 100 ml of methanol having dissolved therein 3.8 g of potassium hydroxide and the mixture was stirred at room temperature for 30 minutes followed by removing methanol under reduced pressure. Benzene was added to the residue to form crystals and then benzene was removed by evaporation. The residue thus-obtained was suspended in 50 ml of dimethylformamide and 10.6 g of methanesulfonyl chloride was added dropwise to the suspension while ice-cooling with stirring. After adding 3.5 g of methanesulfonyl chloride the resulting mixture was stirred at room temperature for 4 hours. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified through silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform). Recrystallization of the elute from water-containing ethanol gave 5.7 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril as colorless prismatic crystals having a melting point of 227° to 231° C.

Workup

  1. dissolutiondissolved
  2. customby removing methanol under reduced pressure
  3. additionBenzene was added to the residue
  4. customto form crystals
  5. custombenzene was removed by evaporation
  6. customThe residue thus-obtained
  7. temperaturecooling
  8. stirringwas stirred at room temperature for 4 hours
  9. customAfter the completion of the reaction
  10. customthe solvent was removed under reduced pressure
  11. customthe residue was purified through silica gel column chromatography (silica gel
  12. customRecrystallization of the
  13. washelute from water-
  14. additioncontaining ethanol

Sources & evidence

ORD record
ord-2c2cec8f0598424e8952ca4587d01ea6
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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