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

HRID 2399877ノート

反応式

HRID 2399877 の反応式
[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]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 12692874HCID 12692874、化合物

生成物 2

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d079cdae7c404bd5920949cafa2521f7
出典データセット
uspto-grants-1995_09
特許番号
US05451677

反応ノート

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