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

HRID 536462Notes

Reaction equation

HRID 536462 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].[CH3:21]N(C=O)C.C(=O)([O-])[O-].[K+].[K+].CI>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

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469560HCID 178469560, compound

Product 1

HCID 20028483Ethyl 1-methyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (10.0 g, 35.1 mmol), DMF (50 mL), potassium carbonate (12.11 g, 88.00 mmol), and methyl iodide (11.00 ml, 175.0 mmol) was heated to 90° C. After 20 minutes, the dark solution was cooled to room temperature and water (25 mL) was added slowly, keeping the temperature <40° C. The reaction mixture was cooled to ambient temperature, and the brown slurry was filtered and washed with 2:1 DMF/water (20 mL×2) and water (20 mL×2). The solids were partially dried on the frit giving the title compound (11.0 g, 36.8 mmol, 105% yield), which was used without further purification in the next step.

Workup

  1. customthe temperature <40° C
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationthe brown slurry was filtered
  4. washwashed with 2:1 DMF/water (20 mL×2) and water (20 mL×2)
  5. customThe solids were partially dried on the frit

Sources & evidence

ORD record
ord-fbeb7f023cb743bc88ab47ef46936d85
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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