Hydrochloric Acid → 3-(Dimethylamino)-7-methoxy-1,2,3,4-tetrahydrocarbazole

HRID 461559

Reaktionsgleichung

Reaktionsgleichung von HRID 461559
[CH3:1][N:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)[CH3:3].Cl.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:20]N)[CH:17]=[CH:18][CH:19]=1.Cl>C(O)C>[CH3:1][N:2]([CH3:3])[CH:4]1[CH2:9][C:8]2[C:17]3[C:16](=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=3)[NH:20][C:7]=2[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1388872-(Dimethylamino)cyclohexan-1-oneHCID 27239403-Methoxyphenylhydrazine hydrochloride

Produkt 1

HCID 123618403-(Dimethylamino)-7-methoxy-1,2,3,4-tetrahydrocarbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 7 g. of dimethylaminocyclohexanone and 8.4 g. of 3-methoxyphenylhydrazine hydrochloride in 40 ml. of absolute ethyl alcohol and 12 ml. of 4-N hydrogen chloride in ethyl alcohol was heated under reflux for two hours. The reaction mixture was allowed to stand for sixteen hours, filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was taken up in water, made alkaline with dilute sodium hydroxide and extracted with ether. The ether extract was washed with water, dried, ethereal hydrogen chloride was added, and the resulting oily precipitate was collected by decantation, recrystallized twice from isopropyl alcohol, suspended in chloroform and treated with dilute sodium hydroxide. The chloroform extract was evaporated to dryness under reduced pressure to give 3-(dimethylamino)-7-methoxy-1,2,3,4-tetrahydrocarbazole, m.p. 100°-105° C.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. waitto stand for sixteen hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. customdried
  9. additionethereal hydrogen chloride was added
  10. customthe resulting oily precipitate was collected by decantation
  11. customrecrystallized twice from isopropyl alcohol
  12. additiontreated with dilute sodium hydroxide
  13. extractionThe chloroform extract
  14. customwas evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-de677e1a6ce8451ea6d3c1aaf616332d
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04062864

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