Diethyl Sulfate → 1-Ethyl-6-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 2059297Notes

Reaction equation

HRID 2059297 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2.S(OCC)(O[CH2:19][CH3:20])(=O)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(Cl)Cl>[CH2:19]([N:10]1[C:11]2[C:6](=[CH:5][C:4]([CH3:3])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14])[CH3:20]

Participants

7

Reactant 3

HCID 6163Diethyl Sulfate2×HCID 14798Sodium Hydroxide2×HCID 152705756-Methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 127821221-Ethyl-6-methyl-1,2,3,4-tetrahydroquinolin-2-oneYield 83.4%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.4 g of benzyltriethyl ammoniumchloride (TEBA) and a solution of 12 g of sodium hydroxide in 12 ml of water are added with stirring to a solution of 9.6 g of 6-methyl-1,2,3,4-tetrahydroquinolin-2-one in 150 ml of methylene chloride. After 20 minutes 23.2 g of diethyl sulphate are added slowly dropwise; stirring is effected for 20 hours, the last 4 hours under reflux. Excess diethyl sulphate is decomposed by addition of 100 ml of 4 N sodium hydroxide solution. One acidifies and extracts for several times with methylene chloride. The organic phase is dried and concentrated and the residue is purified by chromatography over silica gel (eluent: methylene chloride). 9.4 g (83% of theory) of 1-ethyl-6-methyl-1,2,3,4-tetrahydroquinolin-2-one are obtained as oil.

Workup

  1. temperaturethe last 4 hours under reflux
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customthe residue is purified by chromatography over silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-084c11b6001e42ab8d6e14fd57f80ec8
Source dataset
uspto-grants-1982_03
Patent number
US04322439

Reaction notes

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