Hydroxylamine → N-Hydroxy-6-methyl-nicotinamidine

HRID 450597

Reaktionsgleichung

Reaktionsgleichung von HRID 450597
[NH2:1][OH:2].[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1>C(O)C>[OH:2][N:1]=[C:8]([NH2:9])[C:7]1[CH:10]=[CH:11][C:4]([CH3:3])=[N:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 787HydroxylamineHCID 2819956-Methylpyridine-3-carbonitrile

Produkt 1

HCID 73867086N-Hydroxy-6-methyl-nicotinamidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Hydroxylamine (Aldrich, 0.765 g, 10 mmol) in ethanol (10 mL) was treated with a solution 6-methylnicotinonitrile (Aldrich, 12.8 g, 100 mmol) in ethanol (10 mL). The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed under vacuum and the residue was purified with flash column chromatography (5% methanol/dichloromethane) give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 2.2 (s, 3 H), 6.02 (bs, 2 H), 7.59 (m, 1 H), 8.06-8.0 (m, 2 H), 10.2 (s, 1 H) ppm; MS (DCI/NH3) m/z 152 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified with flash column chromatography (5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0b73b99fc48b4d9aa5572b72fca6bbb9
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486979B2

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