Aluminium lithium hydride → HCID 22677536, Verbindung

HRID 378776

Reaktionsgleichung

Reaktionsgleichung von HRID 378776
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]([Cl:18])=[C:10]([N+:19]([O-])=O)[CH:9]=1.O.[NH4+].[OH-]>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[NH2:19][C:10]1[CH:9]=[C:8]([Br:7])[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]=1[Cl:18]

Komponenten

6

Edukt 3

HCID 21226445Aluminium lithium hydrideHCID 21696610HCID 21696610, VerbindungHCID 86589665Water ammonium hydroxide

Produkt 1

HCID 22677536HCID 22677536, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of titanium tetrachloride (0.015 mol, 2.8 g) in tetrahydrofuran (50 mL) was added lithium aluminum hydride (0.0175 mol, 0.7 g). The black slurry was stirred 15 min before adding methyl 6-bromo-3-chloro-4-nitropyridine-2-carboxylate, N-oxide (0.007 mol, 2.3 g) in THF (25 mL). The solution was stirred 1 hr before pouring into 1:1 H2O/NH4OH and filtering. The filtrate was extracted with EtOAc (2×75 mL). The organic phase was dried (Na2SO4), and concentrated. The red solid was chromatographed over silica in 4:1 EtOAc/hexane to give methyl 4-amino-6-bromo-3-chloropyridine-2-carboxylate (0.003 mol, 0.8 g); mp 194-5° C. 1H NMR(CDCl3): δ 3.95 (3H, s), 5.3 (2H, bs), 6.9 (1H, s).

Aufarbeitung

  1. stirringThe solution was stirred 1 hr
  2. filtrationfiltering
  3. extractionThe filtrate was extracted with EtOAc (2×75 mL)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe red solid was chromatographed over silica in 4:1 EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7c6086651c14412d9ff26ab9dd4627c3
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297197B1

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