Aluminum(III) Chloride → 6-Fluoroisoquinoline

HRID 2370720Notes

Reaction equation

HRID 2370720 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].CO[CH:7](OC)[CH2:8][N:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)S(C1C=CC(C)=CC=1)(=O)=O>ClC(Cl)C>[F:27][C:24]1[CH:23]=[C:22]2[C:21](=[CH:26][CH:25]=1)[CH:20]=[N:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59818264N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide

Product 1

HCID 218898476-FluoroisoquinolineYield 29.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

41.6 g AlCl3 were suspended in 400 ml of dichloroethane. At room temperature, a solution of 22.95 g of N-(2,2-dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide (4) in 150 ml of dichloroethane was added. Stirring was continued at room temperature overnight, the solution was poured on ice, the organic layer was separated, the aqueous phase was extracted twice with dichloromethane and the combined organic layers were then extracted twice with sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, evaporated to dryness and the obtained crude product (8.75 g) was purified by silica gel chromatography to yield 2.74 g of 5. Rt=0.30 min (Method #4). Detected mass: 148.1 (M+H+).

Workup

  1. additionthe solution was poured on ice
  2. customthe organic layer was separated
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. extractionthe combined organic layers were then extracted twice with sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated to dryness
  7. customthe obtained crude product (8.75 g)
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-51796681a0594f9ba8d692a870675481
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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