Methyl iodide → 1-Methyl-3,4-dihydroquinolin-2(1H)-one

HRID 620012Notes

Reaction equation

HRID 620012 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3].[OH-].[K+].[CH3:14]I>CS(C)=O.C(Cl)(Cl)Cl>[CH3:14][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3]

Participants

6

Reactant 3

HCID 6328Methyl iodide3×HCID 14797Potassium HydroxideHCID 64796Hydrocarbostyril

Product 1

HCID 5765131-Methyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 6212ChloroformSolvent

Procedure

A solution of 3,4-dihydrocarbostyril (20 g) in DMSO (100 ml) is added to a suspension of KOH (31.4 g) in DMSO (50 ml). Methyl iodide (39.7 g) in DMSO (25 ml) is added to the reaction mixture and the mixture is stirred under an atmosphere of N2 at RT. After 2 hours a second portion of methyl iodide (20 g) is added and after 3 hours a third portion of methyl iodide (20 g) is added and stirring continued for 4.5 hours. The reaction mixture is diluted with chloroform (200 ml), quenched with sat'd aq. NH4Cl, separated, extracted with chloroform, washed with H2O and dried. The organic extracts are filtered and concentrated in vacuo affording the desired product as an oil.

Workup

  1. additionis added
  2. stirringstirring
  3. customquenched with sat'd aq. NH4Cl
  4. customseparated
  5. extractionextracted with chloroform
  6. washwashed with H2O
  7. customdried
  8. filtrationThe organic extracts are filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-173db87c984a49c2b86bd9541026286b
Source dataset
uspto-grants-1989_04
Patent number
US04818755

Reaction notes

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