Acetic Acid → 5-Methanesulfonyloxy-1,2,3,4-tetrahydroquinoline

HRID 1649419Notes

Reaction equation

HRID 1649419 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10](=O)[NH:11]2)(=[O:4])=[O:3].[BH4-].[Na+].C(O)(=O)C>O1CCOCC1>[CH3:1][S:2]([O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][NH:11]2)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 128996762-Oxo-1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate

Product 1

HCID 128996785-Methanesulfonyloxy-1,2,3,4-tetrahydroquinolineYield 44.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.5 g of 5-methanesulfonyloxy-3,4-dihydrocarbostyril was suspended in 90 ml of dioxane and 35 g of NaBH4 was added to the suspension then 5.3 ml of acetic acid was added dropwise to the mixture. After heat-refluxing the resulting mixture for 1 hour the solvent was removed under reduced pressure. A saturated aqueous solution of sodium bicarbonate was added to the residue to form precipitates which were filtered and washed with chloroform. The filtrate was extracted with chloroform and the chloroform layer was dried over Na2SO4 followed by removing the solvent. The residue was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform) and the eluate thus-obtained was crystallized from petroleum ether. Recrystallization of the crystals thus-obtained from methanol gave 1.9 g of 5-methanesulfonyloxy-1,2,3,4-tetrahydroquinoline, colorless prisms having a melting point of 74° to 76° C.

Workup

  1. temperatureAfter heat-refluxing the resulting mixture for 1 hour the solvent
  2. customwas removed under reduced pressure
  3. additionA saturated aqueous solution of sodium bicarbonate was added to the residue
  4. customto form
  5. customprecipitates which
  6. filtrationwere filtered
  7. washwashed with chloroform
  8. extractionThe filtrate was extracted with chloroform
  9. dry with materialthe chloroform layer was dried over Na2SO4
  10. customby removing the solvent
  11. customThe residue was purified through a silica gel column chromatography (silica gel
  12. customeluent: chloroform) and the eluate thus-obtained
  13. customwas crystallized from petroleum ether
  14. customRecrystallization of the crystals
  15. customthus-obtained from methanol

Sources & evidence

ORD record
ord-11f123434994445ca1977c3562e2aae2
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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