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

HRID 2059298Notes

Reaction equation

HRID 2059298 reaction equation
[CH3:1][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.S(OC)(O[CH3:17])(=O)=O.[OH-].[Na+]>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-].C(Cl)Cl>[CH3:17][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:12]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 152705756-Methyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 205469331,6-Dimethyl-1,2,3,4-tetrahydroquinolin-2-oneYield 98%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 13(b) of 9.6 g of 6-methyl-1,2,3,4-tetrahydroquinolin-2-one are reacted with TEBA and dimethyl sulphate in methylene chloride/50% strength sodium hydroxide solution. After extraction with methylene chloride there are obtained 10.2 g (98% of theory) of 1,6-dimethyl-1,2,3,4-tetrahydroquinolin-2-one as a tough oil. The oil is hydrolysed in aqueous-basic solution analogously to Example 3(b).

Workup

  1. extractionAfter extraction with methylene chloride

Sources & evidence

ORD record
ord-51a4b634f00b4b56b90de80905924797
Source dataset
uspto-grants-1982_03
Patent number
US04322439

Reaction notes

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