N-bromobutanimide → 8-Bromo-7-methoxy-6-methylquinoline

HRID 532842Notes

Reaction equation

HRID 532842 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][CH:6]=[CH:5]2.C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Br:21][C:10]1[C:11]([O:12][CH3:13])=[C:2]([CH3:1])[CH:3]=[C:4]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 593661657-Methoxy-6-methylquinoline

Product 1

HCID 593661888-Bromo-7-methoxy-6-methylquinolineYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 6-methyl-7-methoxy-quinoline (3.0 g, 17.3 mmol) in DMF (20 ml) was added NBS (3.4 g, 19 mmol). The resulting suspension was stirred for 3 h at 60° C. and monitored by LCMS. The reaction mixture was diluted with EtOAc (100 ml) and filtered. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and then purified by flash column chromatography on silica gel to give the desired product (2.9 g, 67%). MS (ES) m/z 251.6 (M+H+).

Workup

  1. filtrationfiltered
  2. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-1293a097435f4c13a444c7ad2bc925e1
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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