Sodium Cyanide → N-(5-Hydroxypyridin-2-yl)acetamide

HRID 2399877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399877
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][N:6]=1)(=[O:3])[CH3:2].[C-]#N.[Na+]>CS(C)=O>[OH-:3].[NH4+:4].[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 8929Sodium CyanideHCID 12692874HCID 12692874, Verbindung

Produkt 2

HCID 14923Ammonium HydroxideHCID 19384998N-(5-Hydroxypyridin-2-yl)acetamideAusbeute 111,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 1.72 g (10.4 mmol) of 2-acetamido-5-methoxypyridine, prepared according to the procedure of J. Lombardino, J. Med. Chem. 1981, 24, 39-42, and 2.54 g (51.8 mmol) of sodium cyanide in 10 mL of DMSO was heated at 165° C. under nitrogen for 48 h. The mixture was concentrated under vacuum to remove the DMSO. Purification by flash chromatography (silica, crude product transferred to column in methanol, then diluted with dichloromethane and eluted with 10% 10:1 methanol:concentrated aqueous ammonium hydroxide in dichloromethane) gave 0.881 g (56%) of the title compound as a brown solid: 1H NMR (400 MHz, CD3OD) δ7.84-7.81 (overlapping d, 2H), 7.19 (dd, 1H, J=2.9, 8.9 Hz), 2.12 (s, 3H).

Aufarbeitung

  1. customprepared
  2. concentrationThe mixture was concentrated under vacuum
  3. customto remove the DMSO
  4. customPurification by flash chromatography (silica, crude product
  5. additiondiluted with dichloromethane
  6. washeluted with 10% 10:1 methanol

Quellen und Nachweise

ORD-Eintrag
ord-d079cdae7c404bd5920949cafa2521f7
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451677

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