Aluminum(III) Chloride → 7-Chloro-6-fluoroisoquinoline

HRID 1255415Notes

Reaction equation

HRID 1255415 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:7]=[C:8]([CH:27]=[CH:28][C:29]=1[F:30])[CH2:9][N:10]([CH2:21][CH:22](OC)OC)S(C1C=CC(C)=CC=1)(=O)=O>ClCCl>[Cl:5][C:6]1[CH:7]=[C:8]2[C:27]([CH:22]=[CH:21][N:10]=[CH:9]2)=[CH:28][C:29]=1[F:30]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59226230HCID 59226230, compound

Product 1

HCID 534189227-Chloro-6-fluoroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

343.6 (2.54 mol) of AlCl3 were suspended in 1.1 l 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 silicagel 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+).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 h
  2. waitAfter standing overnight
  3. additionthe reaction suspension was poured on ice
  4. customthe organic layer was separated
  5. extractionthe aqueous phase was extracted twice with dichloromethane
  6. washThe combined organic layers were washed twice with 1 N NaOH and saturated NaHCO3-solution
  7. dry with materialdried with MgSO4
  8. customevaporated
  9. customThe obtained crude product
  10. customwas purified by silicagel chromatography (heptane/ethyl acetate 1:1), which

Sources & evidence

ORD record
ord-7c301da4a94747cba0a915a20594b653
Source dataset
uspto-grants-2013_06
Patent number
US08461144B2

Reaction notes

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