Aluminum(III) Chloride → 6-Fluoroisoquinoline

HRID 402515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402515
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 218898476-FluoroisoquinolineAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

41.6 g of AlCl3 were suspended in 400 mL of dichloromethane. At room temperature, a solution of 22.95 g N-(2,2-dimethoxy-ethyl)-N-(4-fluoro-benzyl)-4-methyl-benzenesulfonamide (2) in 150 ml of dichloromethane was added. Stirring was continued at room temperature overnight, the solution was poured on ice, the layers were 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 compound 3. Rt=0.30 min (Method C). Detected mass: 148.1 (M+H+).

Aufarbeitung

  1. additionthe solution was poured on ice
  2. customthe layers were 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

Quellen und Nachweise

ORD-Eintrag
ord-62f2171032bb48efbf7abc088f6ba15f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742116B2

Notizen zur Reaktion

Wird geladen…