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

HRID 2399877Notes

Reaction equation

HRID 2399877 reaction equation
[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]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 12692874HCID 12692874, compound

Product 2

HCID 14923Ammonium HydroxideHCID 19384998N-(5-Hydroxypyridin-2-yl)acetamideYield 111.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d079cdae7c404bd5920949cafa2521f7
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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