Azobisisobutyronitrile → HCID 18325118, compound

HRID 1250948Notes

Reaction equation

HRID 1250948 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[C:7]([CH3:17])=[C:6]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[Br:26]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[Br:26][CH2:17][C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][C:10]2[C:5]([C:6]=1[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18325149HCID 18325149, compound

Product 1

HCID 18325118HCID 18325118, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 6-methoxy-4-(4-methoxyphenyl)-3-methylquinoline-2-carboxylate (8.27 g) was dissolved in benzene (100 ml); N-bromosuccinimide (5.24 g) and 2,2′-azobis(isobutyronitrile) (0.40 g) were added; followed by refluxing for 2 hours. After cooling to room temperature, the resulting precipitate was filtered off. The filtrate was diluted with ethyl acetate (100 ml), after which it was washed with 1 N sodium hydroxide and brine successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure; the residue obtained was purified by column chromatography (silica gel: 50 g, eluent: ethyl acetate-hexane=1:2). The crude crystal obtained was recrystallized from ethyl acetate-hexane to yield the title compound (9.93 g) as a colorless needle crystal.

Workup

  1. temperatureby refluxing for 2 hours
  2. filtrationthe resulting precipitate was filtered off
  3. additionThe filtrate was diluted with ethyl acetate (100 ml)
  4. washafter which it was washed with 1 N sodium hydroxide and brine successively
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue obtained
  8. customwas purified by column chromatography (silica gel: 50 g, eluent: ethyl acetate-hexane=1:2)
  9. customThe crude crystal obtained
  10. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ac59d74d383947eb8b3f8d092aff0f70
Source dataset
uspto-grants-2002_01
Patent number
US06340704B1

Reaction notes

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