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

HRID 1731013Notes

Reaction equation

HRID 1731013 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.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1>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

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 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 pH10 by periodic additions of 10% sodium hydroxide solution. The mixture was stirred for 21/2 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 21/2 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-da5a4e59337144cd95f174bfc2425119
Source dataset
uspto-grants-1976_11
Patent number
US03994902

Reaction notes

Loading…