Water → Ethyl 1-(2,2-difluoroethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2243054Notes

Reaction equation

HRID 2243054 reaction equation
C[N:2]([CH3:20])[CH:3]=[C:4]([C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:21][CH:22]([F:25])CN.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[F:21][CH:22]([F:25])[CH2:20][N:2]1[C:12]2[C:11](=[CH:16][C:15]([I:17])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1362742,2-DifluoroethanamineHCID 58801734Ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate

Product 1

HCID 59208381Ethyl 1-(2,2-difluoroethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (335 mg, 0.86 mmol) and 2,2-difluoroethylamine (76 mg, 0.94 mmol) in ethanol (3 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and dissolved in DMF (3 mL). Potassium carbonate (178 mg, 1.28 mmol) was added to the reaction mixture and the reaction was heated to 70° C. for 3 h, then cooled to room temperature and poured into water. The title compound formed a precipitate which was collected by filtration and placed upon lyophilizer overnight to remove residual water. MS (ESP): 408 (M+H+) for C14H12F2INO3; NMR: 1.29 (t, J=7 Hz, 3H), 4.25 (q, J=7 Hz, 2H), 4.96 (m, 2H), 6.50 (t, J=20 Hz, 1H), 7.73 (m, 1H), 8.08 (m, 1H), 8.50 (m, 1H), 8.70 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DMF (3 mL)
  3. temperaturethe reaction was heated to 70° C. for 3 h
  4. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-ba5a3d2bba154d6fa2322e147ba64ecf
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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