Quinone → 7,8,9,10-Tetrahydro-11-(4-pyridyl)-6H-azepino[1,2-a]indole-3-ol

HRID 66823

Reaktionsgleichung

Reaktionsgleichung von HRID 66823
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:3][CH:2]=1.[C:15]1(=O)[CH:20]=[CH:19][C:18](=[O:21])[CH:17]=[CH:16]1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:16](=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[N:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:8]=23)=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 4650QuinoneHCID 705496552-(4-Picolinylidene)1,3,4,5,6,7-hexahydroazepine

Produkt 1

HCID 205291797,8,9,10-Tetrahydro-11-(4-pyridyl)-6H-azepino[1,2-a]indole-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

One hundred and forty-one grams (0.75 mole) of 2-(4-picolinylidene)1,3,4,5,6,7-hexahydroazepine were dissolved in 1000 ml of chloroform and mixed under ice cooling with a solution of 89 g (0.83 mole) of 1,4-benzoquinone in 1000 ml of chloroform added dropwise. After the mixture stood for 24 hours at room temperature, the precipitate formed was filtered, suspended in 500 ml of dimethylformamide, and then heated for two hours to 100° C. After cooling, the suspension was suction filtered and washed with dimethylformamide and acetone, whereby the pure 2-hydroxy-isomer was obtained.

Aufarbeitung

  1. additionadded dropwise
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. temperatureheated for two hours to 100° C
  5. temperatureAfter cooling
  6. filtrationfiltered
  7. washwashed with dimethylformamide and acetone, whereby the pure 2-hydroxy-isomer
  8. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-a85841b2f3f94a06bf8c65be4734c04c
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343811

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