【结 构 式】 |
【分子编号】52802 【品名】1,2-dichloro-3-(chloromethyl)-4-nitrobenzene 【CA登记号】 |
【 分 子 式 】C7H4Cl3NO2 【 分 子 量 】240.4724 【元素组成】C 34.96% H 1.68% Cl 44.23% N 5.82% O 13.31% |
合成路线1
该中间体在本合成路线中的序号:(IV)The nitration of 2,3-dichlorobenzaldehyde (I) with HNO3/H2SO4 gives 2,3-dichloro-6-nitrobenzaldehyde (II), which is reduced with NaBH4 in methanol, yielding 2,3-dichloro-6-nitrobenzyl alcohol (III). The reaction of (III) with SOCl2 and TEA affords the benzyl chloride (IV), which is condensed with glycine ethyl ester (V) by means of TEA to provide the adduct (VI). The reduction of the nitro group of (VI) with SnCl2 in aq. HCl or H2 over PtO2/C in ethanol gives the expected amino derivative (VII), which is cyclized with CN-Br in toluene to yield the iminoquinazoline (VIII). Finally, this compound is further cyclized by means of TEA in water to afford the target imidazoquinazolinone.
【1】 Lang, P.C.; Spencer, R.P.; Yeh, W.-L.; Roth, M.J. (Shire Richwood Inc.); Method for the manufacture of anagrelide. WO 0208228 . |
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) | 14742 | 2,3-dichlorobenzaldehyde | 6334-18-5 | C7H4Cl2O | 详情 | 详情 |
(II) | 52800 | 2,3-dichloro-6-nitrobenzaldehyde | C7H3Cl2NO3 | 详情 | 详情 | |
(III) | 52801 | (2,3-dichloro-6-nitrophenyl)methanol | C7H5Cl2NO3 | 详情 | 详情 | |
(IV) | 52802 | 1,2-dichloro-3-(chloromethyl)-4-nitrobenzene | C7H4Cl3NO2 | 详情 | 详情 | |
(V) | 10309 | ethyl 2-aminoacetate; Glycine ethyl ester | 459-73-4 | C4H9NO2 | 详情 | 详情 |
(VI) | 29086 | ethyl 2-[(2,3-dichloro-6-nitrobenzyl)amino]acetate | C11H12Cl2N2O4 | 详情 | 详情 | |
(VII) | 29087 | ethyl 2-[(6-amino-2,3-dichlorobenzyl)amino]acetate | C11H14Cl2N2O2 | 详情 | 详情 | |
(VIII) | 29088 | ethyl 2-[5,6-dichloro-2-imino-1,4-dihydro-3(2H)-quinazolinyl]acetate | C12H13Cl2N3O2 | 详情 | 详情 |