Phenethyl bromide → HCID 59003046, compound

HRID 561170Notes

Reaction equation

HRID 561170 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:19])=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[N:7]2.C([O-])([O-])=O.[K+].[K+].[C:26]1([CH2:32][CH2:33]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][N:7]2[CH2:33][CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 178469611HCID 178469611, compound

Product 1

HCID 59003046HCID 59003046, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of ethyl 5,6,7-trifluoro-4-hydroxy-3-quinolinecarboxylate (2.00 g, 7.37 mmol), K2CO3 (3.06 g, 22.1 mmo) and 2-phenylethyl bromide (1.50 mL, 11.1 mmol) in DMF (16 mL) was stirred at 90° C. for 27 h and concentrated in vacuo. After dilution of the residue with CHCl3, the mixture washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (EtOAc: MeOH 10:1) gave ethyl 5,6,7-trifluoro-1,4-dihydro-4-oxo-1-(2-phenylethyl)-3-quinolinecarboxylate (913 mg, 33%) as a pale yellow powder.

Workup

  1. concentrationconcentrated in vacuo
  2. washAfter dilution of the residue with CHCl3, the mixture washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9755149be5ff43d086cafb85401052d7
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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