Chloroform → 4-Chloro-6-(bromomethyl)-2-(2-nitrophenyl)quinoline

HRID 341822Notes

Reaction equation

HRID 341822 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH:3]=1.C(Cl)(Cl)Cl.[Br:26]N1C(=O)CCC1=O.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][Br:26])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH:3]=1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 67184N-bromobutanimideHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)HCID 153843984-Chloro-6-methyl-2-(2-nitrophenyl)quinoline

Product 1

HCID 153843994-Chloro-6-(bromomethyl)-2-(2-nitrophenyl)quinolineYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 27.6 g (92.4 mmol) of the 4-chloro-6-methyl-2-(2-nitrophenyl)quinoline obtained in Example 1, 110 ml of chloroform was added. After stirring, 15.6 g (87.8 mmol) of N-bromosuccinimide (NBS) was added thereto. Then, 15 ml of chloroform containing 0.78 g of 2,2'-azobis(2,4-dimethylvaleronitrile) was added dropwise thereto, and the thus-prepared mixture was heated under reflux for 1 hour. After cooling to room temperature, the mixture was poured into 220 ml of water and separated out, and the organic layer was washed with 110 ml of water twice. Next, the washed organic layer was evaporated and dried in an evaporator and recrystallized from toluene to obtain 14.7 g of 4-chloro-6-(bromomethyl)-2-(2-nitrophenyl)quinoline.

Workup

  1. temperaturethe thus-prepared mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customseparated out
  4. washthe organic layer was washed with 110 ml of water twice
  5. customNext, the washed organic layer was evaporated
  6. customdried in an evaporator
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-8b7deb4b71304a3a97a87e62c4d7978a
Source dataset
uspto-grants-1999_01
Patent number
US05856337

Reaction notes

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