N-(6-ethyl-3-methylpyridin-2-yl)acetamide | 146331-16-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(6-ethyl-3-methylpyridin-2-yl)acetamide
• CAS: 146331-16-0
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: NUTHNIYCNQALKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(6-ethyl-3-methylpyridin-2-yl)acetamide 在 sodium hydroxide 作用下， 反应 1.5h， 生成 6-乙基-3-甲基-2-吡啶胺
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021
• 作为产物：
  描述：

  2-Methyl-5-oxoheptanenitrile 在 sodium hydroxide 、 硫酸羟胺 、 乙酰氯 作用下， 反应 6.0h， 生成 N-(6-ethyl-3-methylpyridin-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021

文献信息

• [EN] PROCESS FOR THE PREPARATION OF 2-N-ACYLAMINOPYRIDINES AND 2-AMINOPYRIDINES FROM 5-OXOALKANENITRILE OXIMES
  申请人：DSM N.V.

  公开号：WO1991017979A1

  公开（公告）日：1991-11-28

  (EN) The invention relates to a process for the preparation of 2-N-acylaminopyridines of formula (1), where R1 and R5 = an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group, R2, R3 and R4 = hydrogen, an alkoxy group, an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group and R1 and R2 can together form a cycloalkyl group, which are prepared by treating a 5-oxoalkanenitrile oxime of formula (2), where R1 through R4 have the meanings given above, in the presence of a strong acid, with an acylating agent that contains at least on R5 group with the meaning given above. The invention moreover relates to a process for the preparation of 2-aminopyridines of formula (3), where R1 through R4 have the meanings given above, from said 2-N-acylaminopyridines. The invention moreover relates to the 5-oxoalkanenitrile oximes of formula (2), including those where R1 = H and R2 is an acyl group, the 2-N-acylaminopyridines of formula (1), and the 2-aminopyridines of formula (3).(FR) Procédé de préparation d'acylaminopyridines-N-2 répondant à la formule (1), dans laquelle R1 et R5 représentent un groupe alkyle, cycloalkyle, aryle ou hétéroaryle; R2, R3 et R4 représentent hydrogène ou un groupe alcoxy, aryle, hétéroaryle, alkyle ou cycloalkyle; et R1 et R2 peuvent ensemble former un groupe cycloalkyle; et préparées par le traitement d'une oxime d'oxoalcanenitrile-5 répondant à la formule (2), dans laquelle R1, R2, R3 et R4 sont tels que ci-dessus avec un agent d'acylation contenant au moins un groupe R5 tel que défini ci-dessus, et en présence d'un acide fort. On décrit également un procédé de préparation d'aminopyridines-2 répondant à la formule (3), dans laquelle R1, R2, R3 et R4 sont tels que ci-dessus, à partir desdites acylaminopyridines-N-2. Par ailleurs, on décrit les oximes d'oxoalcanenitrile-5 répondant à la formule (2), y compris celles où R1 est hydrogène et R2 est un groupe acyle, les acylaminopyridines-N-2 répondant à la formule (1), et les aminopyridines-2 répondant à la formule (3).
• Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles
  作者：Robert J. Vijn、Henricus J. Arts、Peter J. Maas、Anna M. Castelijns

  DOI：10.1021/jo00056a021

  日期：1993.2

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).