Reaction #2146760

Reaction equation

AlCl3

N-(3-Chloro-4-fluoro-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzene-sulfonamide

→

title compound

7-Chloro-6-fluoro-isoquinoline

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 5 h
2. 2
   workup.WAITAfter standing overnight
3. 3
   workup.ADDITIONthe reaction suspension was poured on ice
4. 4
   Otherthe organic layer was separated
5. 5
   Extractionthe aqueous phase was extracted twice with dichloromethane
6. 6
   WashThe combined organic layers were washed twice with 1 N NaOH and saturated NaHCO3-solution
7. 7
   Dryingdried with MgSO4
8. 8
   Otherevaporated
9. 9
   OtherThe obtained crude product
10. 10
    Otherwas purified by silica gel chromatography (heptane/ethyl acetate 1:1), which

Procedure

343.6 (2.54 mol) of AlCl3 were suspended in 1.11 of dichloromethane and were stirred for 30 min with a mechanical stirrer. To this suspension, a solution of 204 g (0.51 mol) (N-(3-Chloro-4-fluoro-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzene-sulfonamide (2) was added and the mixture was stirred at room temperature for 5 h. After standing overnight, the reaction suspension was poured on ice, the organic layer was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic layers were washed twice with 1 N NaOH and saturated NaHCO3-solution, dried with MgSO4 and evaporated. The obtained crude product was purified by silica gel chromatography (heptane/ethyl acetate 1:1), which gave 61.3 g of the title compound. Rt=0.73 min (Method B). Detected mass: 182.1 (M+H+).

Source