7-nitro-5,8-dichloroisoquinoline | 1198775-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 7-nitro-5,8-dichloroisoquinoline
• 英文别名: 5,8-Dichloro-7-nitroisoquinoline
• CAS: 1198775-29-9
• 化学式: C₉H₄Cl₂N₂O₂
• 分子量: 243.049
• InChiKey: NEWSYZKPVVHRRA-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188 °C
• 沸点：
  399.3±37.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  7-nitro-5,8-dichloroisoquinoline 在 platinum on carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0~50.0 ℃ 、350.0 kPa 条件下， 以55%的产率得到7-amino-5,8-dichlorotetrahydroisoquinoline
  参考文献：
  名称：

  The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A

  摘要：

  The development of an efficient manufacturing route to 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethyoxy)-benzamide hydrochloride SB-406725A (1) is described. Title synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare similar to 30 kg of SB-406725A (1).

  DOI：

  10.1021/op9002054
• 作为产物：
  描述：

  5,8-二氯异喹啉 在 环丁砜 、 nitronium tetrafluoborate 作用下， 反应 18.0h， 以76%的产率得到7-nitro-5,8-dichloroisoquinoline
  参考文献：
  名称：

  The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A

  摘要：

  The development of an efficient manufacturing route to 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethyoxy)-benzamide hydrochloride SB-406725A (1) is described. Title synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare similar to 30 kg of SB-406725A (1).

  DOI：

  10.1021/op9002054

文献信息

• The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A
  作者：Matthew D. Walker、Benjamin I. Andrews、Andrew J. Burton、Luke D. Humphreys、Gary Kelly、Mark B. Schilling、Peter W. Scott

  DOI：10.1021/op9002054

  日期：2010.1.15

  The development of an efficient manufacturing route to 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethyoxy)-benzamide hydrochloride SB-406725A (1) is described. Title synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare similar to 30 kg of SB-406725A (1).