Phenylhydrazine → 1,2,3,3a,4,5-hexahydro-3a-methyl-6H-pyrido[3,2,1-jk]carbazol-6-one

HRID 65622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65622
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:11](=[O:22])[CH2:12][CH2:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O>C(O)C>[CH3:21][C:14]12[CH2:13][CH2:12][C:11](=[O:22])[N:7]3[C:15]1=[C:16]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=13)[CH2:17][CH2:18][CH2:19]2

Komponenten

4

Edukt 2

HCID 7516PhenylhydrazineHCID 574325Methyl 3-(1-methyl-2-oxocyclohexyl)propanoate

Produkt 1

HCID 122918901,2,3,3a,4,5-hexahydro-3a-methyl-6H-pyrido[3,2,1-jk]carbazol-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of phenylhydrazine (1.08 g), 1-methyl-2-oxocyclohexanepropionic acid methyl ester (1.98 g), described in Example 6, and ethanol is heated at reflux for 3 hr. The mixture is evaporated to dryness keeping the temperature of the mixture at about 40° C. The residue is heated with 200 ml of 10% aqueous sulfuric acid at reflux temperature for 1 hr. The mixture is cooled and extracted with ether. The extract is washed with 10% sodium hydroxide and brine, and then evaporated. The residue is subjected to chromatography on silica gel. Elution with benzene gives 1,2,3,3a,4,5-hexahydro-3a-methyl-6H-pyrido[3,2,1-jk]carbazol-6-one (6, R1 = CH3, R2 and R3 = H, m = 3 and n = 2) mp 93°-95° C. Further elution with 5% ethyl acetate in hexane as the eluant gives the title compound, nmr (CDCl3) δ 1.27 (s, 3H), 3.6 (s, 3H), 7.0-7.6 (m, 4H), 7.9 (b, 1H).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 3 hr
  3. customThe mixture is evaporated to dryness
  4. customat about 40° C
  5. temperatureThe residue is heated with 200 ml of 10% aqueous sulfuric acid
  6. temperatureat reflux temperature for 1 hr
  7. temperatureThe mixture is cooled
  8. extractionextracted with ether
  9. washThe extract is washed with 10% sodium hydroxide and brine
  10. customevaporated
  11. washElution with benzene

Quellen und Nachweise

ORD-Eintrag
ord-c85f73ce534d43e0a486591d66891a0e
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128560

Notizen zur Reaktion

Wird geladen…