HCID 13935125, Verbindung → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((3-methylphenyl)methyl)amino)-

HRID 1904728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904728
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

Komponenten

4

Edukt 2

HCID 13935125HCID 13935125, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 30256141-Acridinol, 1,2,3,4-tetrahydro-9-(((3-methylphenyl)methyl)amino)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3,4-Dihydro-9-(3-methylbenzylamino)acridin-1(2H)-one (3.70 g) was dissolved in 100 ml of dry THF and chilled in ice-water. 1M lithium aluminum hydride in THF (7.0 ml) was added and the reaction stirred 30 minutes in the cold. The reaction mixture was quenched by the sequential addition of 0.5 ml of water, 0.5 ml of 15% sodium hydroxide and 1.5 ml of water. The inorganic salts were filtered from the reaction mixture and the organic phase was evaporated to an oil. Trituration with ether gave a solid that was recrystallized from ethyl acetate/pentane to obtain 3.22 g, mp 133°-134° C.

Aufarbeitung

  1. customThe reaction mixture was quenched by the sequential addition of 0.5 ml of water, 0.5 ml of 15% sodium hydroxide and 1.5 ml of water
  2. filtrationThe inorganic salts were filtered from the reaction mixture
  3. customthe organic phase was evaporated to an oil
  4. customTrituration with ether gave a solid
  5. customthat was recrystallized from ethyl acetate/pentane
  6. customto obtain 3.22 g, mp 133°-134° C.

Quellen und Nachweise

ORD-Eintrag
ord-de44bbe3199042bcac7889219966ca4a
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04839364

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