Benzoyl Peroxide → 7-(Bromomethyl)-4-chloroquinoline-2-carbonitrile

HRID 2422536Notes

Reaction equation

HRID 2422536 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]#[N:14])[CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([Cl:1])=[CH:3][C:4]([C:13]#[N:14])=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 597749194-Chloro-7-methylquinoline-2-carbonitrile

Product 1

HCID 667895247-(Bromomethyl)-4-chloroquinoline-2-carbonitrileYield 91.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-chloro-7-methylquinoline-2-carbonitrile (6.66 g, 33 mmol) in CCl4 (160 mL) was added NBS (6.46 g, 36.3 mmol) and benzoyl peroxide (800 mg, 3.3 mmol). The mixture was heated under reflux overnight, cooled to room temperature and evaporated to dryness. The reaction mixture was purified by flash chromatography on silica gel (eluting solvent: dichloromethane/hexane, 9/1) to provide the title compound (8.46 g). 1HNMR (400 MHz, acetone-d6): δ 8.37 (d, 1H), 8.30 (s, 1H), 8.20 (s, 1H), 8.05 (d, 1H), 4.95 (s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customevaporated to dryness
  4. customThe reaction mixture was purified by flash chromatography on silica gel (eluting solvent: dichloromethane/hexane, 9/1)

Sources & evidence

ORD record
ord-041419abeaf543798516093a1e81fb00
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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