Azobisisobutyronitrile → 2-(Bromomethyl)-6-methoxyquinoline

HRID 1983559Notes

Reaction equation

HRID 1983559 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]([CH3:13])[CH:7]=[CH:6]2.C1C(=O)N([Br:21])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][Br:21])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 706486-Methoxyquinaldine

Product 1

HCID 216180432-(Bromomethyl)-6-methoxyquinolineYield 28%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-methoxy-2-methylquinoline (999 mg, 5.77 mmol), NBS (1.03 g, 5.77 mmol), AIBN (153 mg) and chlorobenzene (10 mL) was stirred at 120° C. for 2 hours, then added with AIBN (153 mg) again and further stirred for 4 hours with heating. The solvent was evaporated under reduced pressure, and then the residue was extracted with ether. The solvent was evaporated, and the residue was recrystallized from ethanol to obtain 6-methoxy-2-bromomethylquinoline as white powder (yield: 400 mg, 1.59 mmol, 28%).

Workup

  1. stirringfurther stirred for 4 hours
  2. temperaturewith heating
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe residue was extracted with ether
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3b91c303edd742d89bf2895792245cd6
Source dataset
uspto-grants-2009_06
Patent number
US07541467B2

Reaction notes

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