Aluminum(III) Chloride → 6-Bromoisoquinoline

HRID 404716

Reaction equation

HRID 404716 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]([CH2:22][CH:23](OC)OC)S(C2C=CC(C)=CC=2)(=O)=O)=[CH:8][CH:7]=1>ClCCl>[Br:5][C:6]1[CH:29]=[C:28]2[C:9](=[CH:8][CH:7]=1)[CH:10]=[N:11][CH:22]=[CH:23]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59226245N-(4-Bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide

Product 1

HCID 3136816-BromoisoquinolineYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mechanically stirred suspension of 95.2 g (699.5 mmol) of AlCl3 in 400 ml of dichloromethane a solution of 59.9 g (139.8 mmol) N-(4-bromo-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzenesulfonamide (2) in 400 ml of dichloromethane was added and the reaction was stirred at room temperature for 4 h. After standing overnight, the reaction mixture was poured onto ice, the organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solutions were washed with 1 N NaOH (2×) and saturated sodium hydrogen carbonate-solution (2×). After drying with magnesium sulfate and evaporation of the solvent, the crude product was purified by silica gel chromatography (heptane/ethyl acetate 1:1) to yield 17.5 g of the title compound. Rt=0.68 min (Method C). Detected mass: 208.1/210.1 (M+H+).

Workup

  1. additionwas added
  2. waitAfter standing overnight
  3. additionthe reaction mixture was poured onto ice
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. washThe combined dichloromethane solutions were washed with 1 N NaOH (2×) and saturated sodium hydrogen carbonate-solution (2×)
  7. dry with materialAfter drying with magnesium sulfate and evaporation of the solvent
  8. customthe crude product was purified by silica gel chromatography (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-5ca587cb64be4699ab076df600d18e12
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Linked notes

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