Dimethyl Sulfate → 6-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

HRID 2072246Notes

Reaction equation

HRID 2072246 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O>O>[CH3:19][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution, prepared by mixing 8.2 g. 6-hydroxy-3,4-dihydrocarbostyril with 50 ml. water containing 2 g. sodium hydroxide, was added dropwise with stirring 8.5 ml. dimethyl sulfate (sp. gr. 1.332). During the course of the addition the resulting mixture was maintained at about pH 10 by periodic additions of 10% sodium hydroxide solution. The mixture was stirred for two and one-half hours at room temperature, filtered and the collected solids were washed thoroughly with water to give after recrystallization from methyl alcohol 6.3 g. 6-methoxy-3,4-dihydrocarbostyril; m.p. 142.5°-143.5° C.

Workup

  1. customTo a solution, prepared
  2. additionby mixing 8.2 g
  3. additionDuring the course of the addition the resulting mixture
  4. stirringThe mixture was stirred for two and one-half hours at room temperature
  5. filtrationfiltered
  6. washthe collected solids were washed thoroughly with water
  7. customto give
  8. customafter recrystallization from methyl alcohol 6.3 g

Sources & evidence

ORD record
ord-8d24590fe1b74a34a15de7e8c272f8ed
Source dataset
uspto-grants-1977_09
Patent number
US04049715

Reaction notes

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