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【结 构 式】 
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【分子编号】17298 【品名】3-[(nitrooxy)methyl]phenol 【CA登记号】 |
【 分 子 式 】C7H7NO4 【 分 子 量 】169.13692 【元素组成】C 49.71% H 4.17% N 8.28% O 37.84% |
合成路线1
该中间体在本合成路线中的序号：(III)A mixture of 3-hydroxybenzyl alcohol (I) with 48% hydrobromic acid in dichloromethane is stirred at room temperature to give the corresponding benzyl bromide (II), which is immediately dissolved in acetonitrile. Silver nitrate is added proportionally to the crude solution (II) at room temperature to obtain derivative (III). A mixture of (III), potassium carbonate and ethyl acetate is cooled under nitrogen at 0 C and slowly treated with a solution of O-acetylsalicyloyl chloride (IV) in ethyl acetate to yield crude NCX-4016. The pure product is obtained by crystallization from isopropyl ether. The three-step prepaation is described in the Scheme 25203601a.
| 【1】 Cirino, G.; et al.; NCX-4016. Drugs Fut 1997, 22, 11, 1231. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 17296 | 3-Hydroxybenzyl alcohol; 3-(hydroxymethyl)phenol | 620-24-6 | C7H8O2 | 详情 | 详情 |
| (II) | 17297 | 3-(bromomethyl)phenol | C7H7BrO | 详情 | 详情 | |
| (III) | 17298 | 3-[(nitrooxy)methyl]phenol | C7H7NO4 | 详情 | 详情 | |
| (IV) | 16900 | 2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride | 5538-51-2 | C9H7ClO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)The title compound was synthesized by two procedures. Indomethacin (I) was coupled with 3-hydroxybenzyl nitrate (II) using DCC to yield the title ester.
| 【1】 Del Soldato, P.; Sannicolo', F. (NicOx SA); Nitric ester derivs. and their use in urinary incontinence and other diseases. JP 2000517332; WO 9809948 . |