Methanesulfonic Acid → 3,5-Diamino-2,6-di(methylamino)pyridine

HRID 267499

Reaktionsgleichung

Reaktionsgleichung von HRID 267499
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]([NH:15][CH3:16])[N:4]=1.CS(O)(=O)=O.[H][H]>[Pd].C.CO>[NH2:9][C:8]1[C:3]([NH:2][CH3:1])=[N:4][C:5]([NH:15][CH3:16])=[C:6]([NH2:12])[CH:7]=1

Komponenten

6

Edukt 3

HCID 6395Methanesulfonic AcidHCID 21554890HCID 21554890, VerbindungHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 203634173,5-Diamino-2,6-di(methylamino)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14818447PalladiumcarbonKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A 250 ml Parr bottle was charged with 2,6-di(methylamino)-3,5-dinitropyridine (20.0 g, 0.088 mole), 30 ml methanesulfonic acid, 200 ml methanol and 1.0 g 5% Pd/charcoal catalyst. The mixture was subjected to hydrogenation at ambient temperature with an initial hydrogen pressure of 65 psig. When no further uptake of hydrogen was observed, the mixture was treated with anhydrous silica gel (25 g), filtered free of catalyst and drying agent under a nitrogen atmosphere, and methanol removed under vacuum. The trimethanesulfonate salt of 3,5-diamino-2,6-di(methylamino)pyridine was obtained under nitrogen by addition of cold i-butanol-benzene to the concentrate, followed by vacuum drying (40°-50°C) over P2O5.

Aufarbeitung

  1. additionthe mixture was treated with anhydrous silica gel (25 g)
  2. filtrationfiltered free of catalyst
  3. customdrying agent under a nitrogen atmosphere
  4. custommethanol removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-20dcc80e347542b598402949fe9e27c7
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03943125

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