N-(4-chloro-2-ethoxyphenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-chloro-2-ethoxyphenyl)acetamide
• 英文别名: acetic acid-(2-ethoxy-4-chloro-anilide)；Essigsaeure-(2-aethoxy-4-chlor-anilid)；5-Chlor-2-acetamino-phenol-aethylaether；5-Chlor-2-acetamino-phenetol；4-Chloro-o-acetophenetide
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: HVJQMYZZVGKTME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chloro-2-ethoxyphenyl)acetamide 在 aluminum (III) chloride 、 氨 、 溴 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸酐 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 N-(3-氰基-7-乙氧基-4-羟基喹啉-6-基)乙酰胺
  参考文献：
  名称：

  New Synthesis of N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide

  摘要：

  New synthetic route of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (1) is described on a hectogram scale. The key steps include the intramolecular cyclization of 3-amino-2-(2-chlorobenzoyl)acrylonitrile 22 to give the 3-cyano-4-quinolone 7, which was chlorinated by POCl3 to give the final product 1 in 36.9% yield over 9 steps and 98.9% purity (HPLC). Purification methods of 7 and 1 were also given.

  DOI：

  10.3987/com-13-12830
• 作为产物：
  描述：

  2-氨基-5-氯苯酚 在 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-(4-chloro-2-ethoxyphenyl)acetamide
  参考文献：
  名称：

  New Synthesis of N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide

  摘要：

  New synthetic route of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (1) is described on a hectogram scale. The key steps include the intramolecular cyclization of 3-amino-2-(2-chlorobenzoyl)acrylonitrile 22 to give the 3-cyano-4-quinolone 7, which was chlorinated by POCl3 to give the final product 1 in 36.9% yield over 9 steps and 98.9% purity (HPLC). Purification methods of 7 and 1 were also given.

  DOI：

  10.3987/com-13-12830

文献信息

• XII.—A new method of reducing aromatic nitro-compounds
  作者：Theodora Elizabeth de Kiewiet、Henry Stephen

  DOI：10.1039/jr9310000082

  日期：——
• Orton; King, Journal of the Chemical Society, 1911, vol. 99, p. 1188
  作者：Orton、King

  DOI：——

  日期：——
• Orton; King, Journal of the Chemical Society, 1911, vol. 99, p. 1372
  作者：Orton、King

  DOI：——

  日期：——
• Mangini; Deliddo, Gazzetta Chimica Italiana, 1933, vol. 63, p. 612,620
  作者：Mangini、Deliddo

  DOI：——

  日期：——
• New Synthesis of N-(4-Chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide
  作者：Jianfeng Li、Yongjun Mao、Yang He、Fuqiang Zhu、Weiming Chen、Jingshan Shen

  DOI：10.3987/com-13-12830

  日期：——

  New synthetic route of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetamide (1) is described on a hectogram scale. The key steps include the intramolecular cyclization of 3-amino-2-(2-chlorobenzoyl)acrylonitrile 22 to give the 3-cyano-4-quinolone 7, which was chlorinated by POCl3 to give the final product 1 in 36.9% yield over 9 steps and 98.9% purity (HPLC). Purification methods of 7 and 1 were also given.