Aluminum(III) Chloride → 6-Bromoisoquinoline

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+).

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)

ORDレコード

ord-5ca587cb64be4699ab076df600d18e12

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08748614B2