Hydrochloric Acid → 1-(2,3-Dihydro-1H-indol-7-yl)ethan-1-one

HRID 414414

Reaktionsgleichung

Reaktionsgleichung von HRID 414414
B(Br)(Br)Br.[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.[C:14](#N)[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH2:22]>C1(C)C=CC=CC=1>[C:14]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[NH:5][CH2:6][CH2:7]2)(=[O:22])[CH3:15]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 6342AcetonitrileHCID 10328IndolineHCID 25134Boron tribromideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 136994211-(2,3-Dihydro-1H-indol-7-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 47.35 g. (0.5 mole) of boron tribromide in 300 ml. of toluene at 0° C. was added dropwise a solution of 50 g. (0.42 mole) of indoline and 22.39 g. (0.546 mole) of acetonitrile in 200 ml. of toluene. After stirring for 10 minutes 67.2 g. (0.5 mole) of aluminum chloride was added in portions. The resulting reaction mixture was heated to reflux for 66 hours, cooled to 5° C. and treated with 80 ml. of water and 330 ml. of 2N hydrochloric acid. The resulting mixture was heated to reflux for 2.5 hours, cooled and filtered. The filtrate was set aside and the solids suspended in 500 ml. of water and treated with 2N sodium hydroxide solution until basic. The basic mixture wa extracted (2×200 ml.) with methylene chloride and the organic phase separated, dried and concentrated to a solid, 17.2 g. The filtrate which was set aside was made basic with 4N aqueous sodium hydroxide and extracted with methylene chloride. The organic phase was separated, dried and concentrated to a solid, 21.8 g. The combined solids were recrystallized from hexane, 30 g., m.p. 83°-85° C.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 66 hours
  4. additiontreated with 80 ml
  5. temperatureThe resulting mixture was heated
  6. temperatureto reflux for 2.5 hours
  7. temperaturecooled
  8. filtrationfiltered
  9. additionof water and treated with 2N sodium hydroxide solution until basic
  10. extractionThe basic mixture wa extracted (2×200 ml.) with methylene chloride
  11. customthe organic phase separated
  12. customdried
  13. concentrationconcentrated to a solid, 17.2 g
  14. extractionextracted with methylene chloride
  15. customThe organic phase was separated
  16. customdried
  17. concentrationconcentrated to a solid, 21.8 g
  18. customThe combined solids were recrystallized from hexane, 30 g

Quellen und Nachweise

ORD-Eintrag
ord-ac44012fb0834c0b9ac3d45f9787f0a1
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791129

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