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

HRID 2399877노트

반응식

HRID 2399877 반응식
[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]

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 12692874HCID 12692874, 화합물

생성물 2

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d079cdae7c404bd5920949cafa2521f7
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05451677

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