Water → Ethyl 6-iodo-1-[2-(methyloxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate

HRID 2061853Notes

Reaction equation

HRID 2061853 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].[CH3:21][O:22][CH2:23]CN.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[I:17][C:15]1[CH:16]=[C:11]2[C:12](=[CH:13][CH:14]=1)[N:2]([CH2:20][CH2:21][O:22][CH3:23])[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]2=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 70809441(Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate2×

Product 1

HCID 59208478Ethyl 6-iodo-1-[2-(methyloxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylateYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

(Z)-Ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (0.428 g, 1.09 mmol, Intermediate 24) and 2-methoxyethanamine (0.082 g, 1.09 mmol, Acros) were combined in DMF (3.0 mL). Potassium carbonate (0.151 g, 1.09 mmol, Fisher) was added and the reaction was heated in the microwave at 90° C. for 30 min After 30 minutes, LC/MS indicated that the reaction was complete. The reaction mixture was cooled to room temperature and slowly poured into water. The resulting precipitate was filtered, washed with water and dried overnight to yield a white solid (0.277 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried overnight

Sources & evidence

ORD record
ord-2981c7356ea54766a3bc4b1b425491b1
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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