Water → HCID 10797271, Verbindung

HRID 2229305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229305
Cl[Sn]Cl.O.[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH2:13][CH3:14])[C:9]([N+:15]([O-])=O)=[CH:8][CH:7]=1.O.[OH-].[Na+]>Cl.CC(O)=O>[NH2:15][C:9]1[C:10]([NH:12][CH2:13][CH3:14])=[N:11][C:6]([Cl:5])=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 107267696-Chloro-N-ethyl-3-nitropyridin-2-amineHCID 43835034Tin dichloride dihydrate

Produkt 1

HCID 10797271HCID 10797271, VerbindungAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of SnCl2.H2O (616.3 g, 2.73 mol) in aqueous 12 N HCl (500 mL) was rapidly added to a solution of 6-chloro-2-(ethylamino)-3-nitropyridine (169.5 g, 0.84 mol) in AcOH (1.7 L) at room temperature. After 20 min, the mixture was cooled to 0° C. and water (250 mL) was added. Solid NaOH (240 g) was then added in small portions. The resulting suspension was filtered to remove tin salts. The filtrate was diluted with water (3.5 L), the solution rendered basic by addition of aqueous 10 N NaOH and then extracted with EtOAc (3×1.7 L). The combined organic layers were washed with brine (1 L), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 3:2) to give the title compound (89.9 g, 62% yield) as a brown solid: MS (ESI) m/z 172/174 (MH)+.

Aufarbeitung

  1. filtrationThe resulting suspension was filtered
  2. customto remove tin salts
  3. additionThe filtrate was diluted with water (3.5 L)
  4. additionthe solution rendered basic by addition of aqueous 10 N NaOH
  5. extractionextracted with EtOAc (3×1.7 L)
  6. washThe combined organic layers were washed with brine (1 L)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (hexane:EtOAc, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-46f38614edda4eb6be528a31ad0b3ddc
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420359B1

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