Water → HCID 391101, Verbindung

HRID 1683877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683877
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:19][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][C:14](=O)[C:13]3=O)=[C:8]2[CH2:7][CH2:6]1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:19][C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][CH:14]=[CH:13]3)=[C:8]2[CH2:7][CH2:6]1)[CH2:21][CH3:22]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19041527HCID 19041527, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 391101HCID 391101, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 7-di-n-propylamino-6,7,8,9-tetrahydro-1H-benzo[g]indole-2,3-dione, 2a, (Chart 1) (22.0 g, 73.2 mmol) in dry diethyl ether (100 mL) was added dropwise to a suspension of lithiumaluminum hydride (9.0 g, 237 mmol) in dry diethyl ether (600 mL). After stirring overnight at ambient temperature, water (9.0 mL), 15% sodium hydroxide (9 mL) and water (27 mL) were consecutively added. The mixture was stirred for 20 minutes followed by filtration of inorganic material. The solution was dried (sodium sulfate), filtered and evaporated to yield 17 g of a blue off, which was purified on silica (acetone/methanol, 20:1) to yield 7.4 g (37%) of the pure material. For analytical and biological purposes, the fumarate salt (1/2 fum) was prepared which was recrystallized from ethanol/diethyl ether. m.p. 201°-205° C.

Aufarbeitung

  1. stirringThe mixture was stirred for 20 minutes
  2. filtrationfollowed by filtration of inorganic material
  3. dry with materialThe solution was dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customto yield 17 g of a blue off, which
  7. customwas purified on silica (acetone/methanol, 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-1dbfd13314bb4d2cbcb8167c94d2a5cb
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639778

Notizen zur Reaktion

Wird geladen…