Dimethylformamide → 3-Benzyl-4-(6-bromohexyloxy)-8-(trifluoromethyl)quinoline

HRID 1677124Notes

Reaction equation

HRID 1677124 reaction equation
CN(C=O)C.[CH2:6]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][C:17]=2[C:24]([F:27])([F:26])[F:25])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[O:23][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][Br:28])=[CH:20][CH:19]=[CH:18][C:17]=2[C:24]([F:27])([F:25])[F:26])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 178515542HCID 178515542, compound

Product 1

HCID 668707273-Benzyl-4-(6-bromohexyloxy)-8-(trifluoromethyl)quinolineYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF (3 mL) solution of 3-benzyl-8-(trifluoromethyl)quinolin-4-ol (500 mg, 1.65 mmol), 1,6-dibromohexane (3.22 g, 13.20 mmol), and potassium carbonate (455.7 mg, 3.30 mmol) was stirred at room temperature overnight. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane:ethyl acetate), and the title compound (660 mg, yield 86%) was obtained as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-679d1fe8ff274aac8f0a1803a70366b1
Source dataset
uspto-grants-2011_08
Patent number
US08008306B2

Reaction notes

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