HCID 14253836, Verbindung → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

HRID 580728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580728
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[C:18](=[O:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[CH:18]([OH:20])[CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

4

Edukt 2

HCID 14253836HCID 14253836, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 30256131-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3,4-Dihydro-9-(2-methylbenzylamino)acridin-1(2H)-one (4.15 g) was suspended in 100 ml of THF and chilled with ice-water. 1M lithium aluminum hydride in THF (8.0 ml) was added dropwise through a syringe and then the reaction mixture was stirred 30 minutes in the cold. It 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 and the organic phase was evaporated to obtain an amorphous solid product. Recrystallization from ethyl acetate gave 3.38 g, mp 167°-169° C.

Aufarbeitung

  1. customIt 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
  3. customthe organic phase was evaporated
  4. customto obtain an amorphous solid product
  5. customRecrystallization from ethyl acetate
  6. customgave 3.38 g, mp 167°-169° C.

Quellen und Nachweise

ORD-Eintrag
ord-89eabfb76c114cf18f9e22b83b18ff81
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04754050

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