Azobisisobutyronitrile → Ethyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 964574Notes

Reaction equation

HRID 964574 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:30])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[CH:13][C:12]([O:26][CH3:27])=[C:11]([O:28][CH3:29])[CH:10]=2)=[O:5])[CH3:2].[Br:31]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH2:30][Br:31])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[CH:13][C:12]([O:26][CH3:27])=[C:11]([O:28][CH3:29])[CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19032371Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate

Product 1

HCID 21851143Ethyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-methylquinoline-3-carboxylic acid ethyl ester (411 mg), N-bromosuccinimide (214 mg), 2,2'-azobis(isobutyronitrile) (10 mg) and carbon tetrachloride (10 ml) was stirred under refluxing conditions for 5 hours. The reaction mixture was washed with water and dried (MgSO4), after which the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (10:1, v/v) to yield 2-bromomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester (285 mg, 58%), which was then recrystallized from ethyl acetate-hexane to yield a colorless prismatic crystal having a melting point of 135° to 136° C.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. distillationafter which the solvent was distilled off under reduced pressure
  4. washeluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record
ord-d47f27e177df45c7bebd027dd88bfe0e
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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