Methyl iodide → 6-Methoxy-1,2,3,4-tetrahydroquinolin-2-one

HRID 2386170Notes

Reaction equation

HRID 2386170 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.[C:13]([O-])([O-])=O.[K+].[K+].CI>CN(C)C=O>[CH3:13][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 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 108884676-Methoxy-1,2,3,4-tetrahydroquinolin-2-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Hydroxy-3,4-dihydroquinolin-2(1H)-one (18.38 mmol, 3.00 g) was treated in the presence of K2CO3 (22.98 mmol, 3.18 g) with methyl iodide (22.98 mmol, 3.26 g) in N,N-dimethylformamide (30 ml) at room temperature for 24 hours, resulting in 2.05 g of the title compound.

Sources & evidence

ORD record
ord-76513a97224341189ff7e5245f536870
Source dataset
uspto-grants-2012_09
Patent number
US08268815B2

Reaction notes

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