Aluminum(III) Chloride → 6-Fluoroisoquinoline

HRID 1022865Notes

Reaction equation

HRID 1022865 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>ClCCl>[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 6344DichloromethaneSolvent2×

Procedure

41.6 g of AlCl3 were suspended in 400 mL of dichloromethane. At room temperature, a solution of 22.95 g of N-(2,2-Dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide (22) in 150 ml of dichloromethane 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 are then extracted twice with sodium bicarbonate. The organic layer was dried over magnesium sulfate, evaporated to dryness and the obtained crude product (8.75 g) is purified by silica gel chromatography to yield 2.74 g of compound 23. 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 are then extracted twice with sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated to dryness
  7. customthe obtained crude product (8.75 g)
  8. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-7325a68b6d614c34a6ff5d3d6fb44c6c
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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