Azobisisobutyronitrile → 7-(Bromomethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422525Notes

Reaction equation

HRID 2422525 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 574378317-Methyl-4-phenylquinoline-2-carbonitrile

Product 1

HCID 574378327-(Bromomethyl)-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 7-methyl-4-phenylquinoline-2-carbonitrile (11.2 g, 41.7 mmol), N-bromo-succinimide (12.2 g, 68.6 mmol) and AIBN (2,2′-azobisisobutyronitrile) (200 mg) in carbon tetrachloride (200 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and the solid residue was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by flash column chromatography (eluting with 5% ethyl acetate in hexane) to give the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.30 (s, 1H), 8.06 (d, 1H), 7.90 (s, 1H), 7.87 (d, 1H), 7.6-7.7 (m, 5H), 4.95 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. filtrationthe solid residue was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash column chromatography (eluting with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ad51e95d5f2a4fe887226f09a875a790
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…