Sodium Carbonate → 4-Bromo-3-methyl-isoquinoline

HRID 1836306Notes

Reaction equation

HRID 1836306 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:12]Br.C(=O)([O-])[O-].[Na+].[Na+]>[N+](C1C=CC=CC=1)([O-])=O>[Br:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 143063-MethylisoquinolineHCID 24408Bromine

Product 1

HCID 37777034-Bromo-3-methyl-isoquinolineYield 72.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

To 3-methylisoquinoline (0.500 g, 3.49 mmol) in 1 ml nitrobenzene, bromine (0.196 ml, 3.84 mmol) was added and the contents heated in a sealed tube at 180° C. for 4 hours. The solution was cooled to room temperature, neutralized with solid sodium carbonate (pH=8) and extracted with ethyl acetate (2×20 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified (hexane:EtOAc; 4.5:0.5) to give 0.560 g (72%) of the product as syrup.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customcolumn purified (hexane:EtOAc; 4.5:0.5)

Sources & evidence

ORD record
ord-dd99a739806f43e796998e1b36f4a0a0
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

Loading…