Methyl iodide → Ethyl 1-methyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

HRID 1722252Notes

Reaction equation

HRID 1722252 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:21](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:21][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:13])[F:14])[CH:7]=2)[C:2](=[O:1])[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469560HCID 178469560, compound

Product 1

HCID 20028483Ethyl 1-methyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of ethyl 4-hydroxy-7-trifluoromethylquinoline-3-carboxylate (370.5 g), anhydrous potassium carbonate (179.4 g), iodomethane (202.4 g) and anhydrous dimethylformamide (2 liters) was stirred at room temperature overnight. More dimethylformamide (500 ml) was added and stirring was continued for 24 hours. The dimethylformamide was distilled off in vacuo and water (2 litres) was added to the residue. The resulting solid was collected, washed with water, dried and recrystallised from IMS to give the novel compound ethyl 1-methyl-4-oxo-7-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate, m.p. 222°-224°.

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. distillationThe dimethylformamide was distilled off in vacuo and water (2 litres)
  4. additionwas added to the residue
  5. customThe resulting solid was collected
  6. washwashed with water
  7. customdried
  8. customrecrystallised from IMS

Sources & evidence

ORD record
ord-38bea017969548c788f63ef306968e04
Source dataset
uspto-grants-1989_08
Patent number
US04855291

Reaction notes

Loading…