Iodoethane → 2-Ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 242111Notes

Reaction equation

HRID 242111 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[C:13]([OH:27])=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8].I[CH2:29][CH3:30].CCOC(C)=O.CCCCCC>CN(C=O)C.O.CCOC(C)=O>[CH2:7]([O:9][C:10]([C:12]1[C:13]([O:27][CH2:29][CH3:30])=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)=[O:11])[CH3:8]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 178470056HCID 178470056, compound

Product 1

HCID 665838422-Ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl esterYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

354 mg (2.6 mmol) K2CO3 was added to a solution of 700 mg (2.3 mmol) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in DMF (9 ml) and stirred for 60 min at RT. 190 μl (2.3 mmol) iodoethane was then added and the RS was stirred for a further 16 h at RT. The solution was subsequently diluted with water and EtOAc. The organic phase was separated, dried over MgSO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:3) of the residue, 168 mg (0.5 mmol, 22%) 2-ethoxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

Workup

  1. stirringthe RS was stirred for a further 16 h at RT
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-3b162fcce91a46c3bf5c42a1997a8950
Source dataset
uspto-grants-2014_02
Patent number
US08653101B2

Reaction notes

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