Methyl iodide → 1-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

HRID 974229Notes

Reaction equation

HRID 974229 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][C:2]1=[O:12].[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:13][N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][C:2]1=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

Product 1

HCID 104422421-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.36 g (0.0206 mol) of 7,8-dihydro-2,5(1H,6H)-quinolinedione are stirred with 5.69 g (2×0.0206 mol) of powdered anhydrous potassium carbonate and 1.92 ml (1.5×0.0206 mol) of methyl iodide in 35 ml of dimethylformamide for 16 hours at ambient temperature. The mixture is then suction filtered, the solvent is evaporated off in vacuo and the residue is recrystallised from chloroform/ethyl acetate. Melting point: 203°-205° C., Yield: 3.1 g (84.9% of theory).

Workup

  1. filtrationsuction filtered
  2. customthe solvent is evaporated off in vacuo
  3. customthe residue is recrystallised from chloroform/ethyl acetate

Sources & evidence

ORD record
ord-cbe45208940749aeb179dd236699155a
Source dataset
uspto-grants-1991_11
Patent number
US05068334

Reaction notes

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