N-bromobutanimide → 8-(1-bromoethyl)quinoline

HRID 1643394Notes

Reaction equation

HRID 1643394 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2)[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2)[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 88185Quinoline, 8-ethyl-

Product 1

HCID 126448138-(1-bromoethyl)quinolineYield 78%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (12) (3.0 g, 19.1 mmol) in carbon tetrachloride (30 mL) was added NBS (5.10 g, 28.6 mmol), and benzoyl peroxide (0.12 g, 0.48 mmol). The mixture was heated at 100° C. for 3 hours. The reaction was cooled to room temperature. The mixture was filtered through filter paper, and washed with ethyl acetate. The filtrate was adsorbed into silica gel. The mixture was purified by chromatography on silica gel with 5 to 15% ethyl acetate in hexane to give 8-(1-bromoethyl)quinoline (13) (3.5 g, 14.8 mmol, 78% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. filtrationthrough filter paper
  4. washwashed with ethyl acetate
  5. customThe mixture was purified by chromatography on silica gel with 5 to 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a74609774a004dd1a250f30eb5ffdf58
Source dataset
uspto-grants-2012_02
Patent number
US08119807B2

Reaction notes

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