Aluminum(III) Chloride → 6-Bromoisoquinoline

HRID 1621282

Reaction equation

HRID 1621282 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) AlCl3 in 400 ml 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 dichloromethane was added and the reaction was stirred at room temperature for 4 h. After standing overnight, the reaction mixture was poured on 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 NaHCO3-solution (2×). After drying with MgSO4 and evaporation of the solvent, the crude product was purified by silicagel 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 on 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 NaHCO3-solution (2×)
  7. dry with materialAfter drying with MgSO4 and evaporation of the solvent
  8. customthe crude product was purified by silicagel chromatography (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-f82307a1177c49c1a1c5d49ca0815f86
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Linked notes

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