Hydroxyamine hydrochloride → 3-Amino-2-(amino(hydroxyimino)methyl)pyridine

HRID 380390

Reaktionsgleichung

Reaktionsgleichung von HRID 380390
[NH2:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].Cl.[NH2:14][OH:15]>C(O)C>[NH2:1][C:2]1[C:3]([C:8]([NH2:9])=[N:14][OH:15])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 5770153-Aminopyridine-2-carbonitrileHCID 10942334Sodium Methoxide

Produkt 1

HCID 1361447773-Amino-2-(amino(hydroxyimino)methyl)pyridineAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 3-amino-2-cyanopyridine (1.18 g, 9.9 mmol), sodium methoxide (0.64 g, 12 mmol) and hydroxylamine hydrochloride (0.83 g, 12 mmol) in ethanol (10 ml) was heated under reflux for 1 h. The mixture was filtered and the filtrate concentrated to an oil, which was purified by flash column chromatography on silica gel, eluting with dichloromethane/methanol (50:1 to 10:1) as eluent to afford the product as a yellow solid (0.82 g), MS (+CI) m/z 153 [M+H]+; 1H NMR (d6-DMSO) 9.80 (1H, br. s), 7.80 (1H, dd), 7.10 (1H, d), 7.08 (1H, d), 6.62 (2H, s), 5.90 (1H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated to an oil, which
  5. customwas purified by flash column chromatography on silica gel
  6. washeluting with dichloromethane/methanol (50:1 to 10:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-63ddb89852df4bd6b059e32a494008ef
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303613B1

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