Potassium Hydroxide → 5-Bromo-6-methoxy-7-methylquinoline

HRID 2207016Notes

Reaction equation

HRID 2207016 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]=[CH:8][CH:7]=[CH:6]2.[Br:14]N1C(=O)CCC1=O.[OH-].[K+]>OS(O)(=O)=O>[Br:14][C:4]1[C:3]([O:2][CH3:1])=[C:12]([CH3:13])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 155348986-Methoxy-7-methylquinoline

Product 1

HCID 666307145-Bromo-6-methoxy-7-methylquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
15 °C

Procedure

To the solution of 6-methoxy-7-methylquinoline (4.28 g, 24.6 mmol) in 50 mL of concentrated H2SO4 was added N-bromosuccinimide (4.41 g, 14.6 mmol) at 15° C., and the reaction was stirred at 15° C. for 3.5 hours. The reaction mixture was poured into ice-water (600 mL). The aqueous mixture was adjusted with a 50% KOH solution to pH ˜10, and then extracted with DCM (3×). The combined extract was dried with sodium sulfate. Concentration under reduced pressure gave 5-bromo-6-methoxy-7-methylquinoline. LCMS-ESI+ (m/z): 252.1, 254.1 (M+H)+.

Workup

  1. extractionextracted with DCM (3×)
  2. extractionThe combined extract
  3. dry with materialwas dried with sodium sulfate
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-5ec83fbf657d4377aa8c656de182dfa7
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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