Methyl iodide → Ethyl 7-bromo-1,4-dihydro-1-methyl-4-oxo-3-quinolinecarboxylate

HRID 963396Notes

Reaction equation

HRID 963396 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469486HCID 178469486, compound

Product 1

HCID 22626890Ethyl 7-bromo-1,4-dihydro-1-methyl-4-oxo-3-quinolinecarboxylateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.04 g of ethyl 7-bromo-4-hydroxy-quinoline-3-carboxylate (J. Am. Chem. Soc. 71,3226, (1949)) and 4.71 g of potassium carbonate in 30 ml of dimethylformamide is treated with 9.68 g of methyl iodide at room temperature. The reaction mixture is heated to 90° and stirred at this temperature for 3 hrs. The reaction mixture is concentrated in a high vacuum. The residue is suspended in 50 ml of water, filtered off under suction and washed with 50 ml of water. Recrystallization of the crude product from ethanol/diethyl ether yields 3.67 g (86%) of ethyl 7-bromo-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 189°-191°.

Workup

  1. temperatureThe reaction mixture is heated to 90°
  2. concentrationThe reaction mixture is concentrated in a high vacuum
  3. filtrationfiltered off under suction
  4. washwashed with 50 ml of water
  5. customRecrystallization of the crude product from ethanol/diethyl ether

Sources & evidence

ORD record
ord-c75ff85619c6403ba82c72d46de430b0
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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