Ethanol → HCID 14612522, compound

HRID 525964Notes

Reaction equation

HRID 525964 reaction equation
CN(C)[CH:3]=[C:4]([C:10](=[O:20])[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1F)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)C.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)C>[C:25]([N:29]1[C:12]2[C:11](=[CH:16][C:15]([F:17])=[C:14]([F:18])[CH:13]=2)[C:10](=[O:20])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1)([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 702EthanolHCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 53640509HCID 53640509, compound

Product 1

HCID 14612522HCID 14612522, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate (64 g, 212 mmol) in a mixed solvent of Ethanol (150 mL)/Diethyl ether (300 mL) was added tert-Butylamine (44.6 mL, 425 mmol), and the reaction mixture was stirred at rt for 2 h. The mixture was concentrated under reduced pressure, the resulting oily residue was dissolved in N,N-Dimethylformamide (DMF) (250 mL) and potassium carbonate (88 g, 637 mmol) was added. LCMS showed completion of the reaction after being stirred at 100° C. for 2 h. Cold water was added to the mixture, and the precipitates were collected by filtration and dried to afford ethyl 1-(tert-butyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (60 g, 194 mmol, 91% yield) as pale yellow solid. LCMS: (M+H)+: 310.1

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting oily residue was dissolved in N,N-Dimethylformamide (DMF) (250 mL)
  3. customcompletion of the reaction
  4. stirringafter being stirred at 100° C. for 2 h
  5. filtrationthe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-cb060dcdd8b84949bb29db3ba4664fe8
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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