bis(6-chloro-3-pyridylmethyl)amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: bis(6-chloro-3-pyridylmethyl)amine
• 英文别名: Bis-(6-chlor-[3]pyridylmethyl)-amin；1-(6-chloropyridin-3-yl)-N-[(6-chloropyridin-3-yl)methyl]methanamine
• 化学式: C₁₂H₁₁Cl₂N₃
• 分子量: 268.145
• InChiKey: XCAQGOMJZJRWQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯-3-氰基吡啶 在 1,2,3,4-四氢萘 、 nickel-copper catalyst 作用下， 生成 bis(6-chloro-3-pyridylmethyl)amine
  参考文献：
  名称：

  Raeth, Justus Liebigs Annalen der Chemie, 1931, vol. 489, p. 107,117

  摘要：

  DOI：

文献信息

• Practical Synthesis of (6-Chloro-3-pyridyl)methylamine by Highly Selective Hydrogenation of 6-Chloro-3-pyridinecarbonitrile with Improved Raney Nickel Catalyst
  作者：Ken Tanaka、Minoru Nagasawa、Hideki Sakamura

  DOI：10.1246/bcsj.73.1227

  日期：2000.5

  A practical synthesis of (6-chloro-3-pyridyl)methylamine (1), one of the key intermediates of neo-nicotinoid insecticides, by a highly selective hydrogenation of 6-chloro-3-pyridinecarbonitrile (4) is described. The use of an improved Raney nickel catalyst, prepared from an alloy of low nickel content (Ni 38%, Al 62%) and subjected to heat treatment in water (98 °C, 2 h) after leaching of aluminum, was highly effective for the selective hydrogenation of 4. The hydrogenation of 4 using this catalyst was carried out in EtOH-H2O [6 : 1 (v/v)] and NH3 at 50 °C and 1.2—1.4 kg cm-2 hydrogen pressure to give 1 in 86% yield and 3-pyridylmethylamine, a dechlorinated by-product, in 2% yield.

  本文描述了一种实用合成（6-氯-3-吡啶基）甲胺（1）的方法，该化合物是新烟碱类杀虫剂的重要中间体，采用对6-氯-3-吡啶腈（4）进行高度选择性的加氢反应。使用改进的Raney镍催化剂，该催化剂由低镍含量合金（镍38%，铝62%）制备，并在浸出铝后在水中进行热处理（98°C, 2小时），对4的选择性加氢反应非常有效。使用该催化剂对4进行加氢反应是在乙醇-水 [6:1 (v/v)] 和氨气的条件下，于50°C和1.2—1.4 kg cm-2的氢气压力下进行的，最终得到1的产率为86%，并生成脱氯副产物3-吡啶基甲胺，产率为2%。
• Highly selective hydrogenation of 2-chloro-5-cyanopyridine with an improved sponge nickel catalyst
  作者：Ken Tanaka、Minoru Nagasawa、Yuzo Kasuga、Hideki Sakamura、Yuki Takuma、Katsuyoshi Iwatani

  DOI：10.1016/s0040-4039(99)01097-7

  日期：1999.8

  A practical synthesis of (6-chloropyridin-3-yl)methylamine (1), a key intermediate of neo-nicotinoide insecticides 2, was achieved by highly selective hydrogenation of 2-chloro-5-cyanopyridine (3). The hydrogenation of 3 with an improved Sponge nickel catalyst, prepared from an alloy of low nickel content (Ni 38%, Al 62%) and subjected to heat treatment in water, wits carried out at 50 degrees C and 1.2-1.4 kg/cm(2) hydrogen pressure to give 1 in 86% yield and (pyridin-3-yl)methylamine (4), a dechlorinated by-product, in only 2% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• JPH07224035A
  申请人：——

  公开号：JPH07224035A

  公开（公告）日：1995-08-22