Lithium hydride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((2-methylphenyl)methyl)amino)-

HRID 1763035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1763035
[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-].[Li+]>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 62714Lithium hydrideHCID 14253836HCID 14253836, Verbindung

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 hydride in THF (8.0 ml) was added dropwise through a syringe and then the reactionh 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.1

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-ade569a3f0bc4ff995db9bef8dce8b4a
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04835275

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