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【结 构 式】 
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【分子编号】27366 【品名】Ethyl hydrazinecarboxylate; Ethyl 1-hydrazinecarboxylate 【CA登记号】4114-31-2 |
【 分 子 式 】C3H8N2O2 【 分 子 量 】104.1088 【元素组成】C 34.61% H 7.75% N 26.91% O 30.74% |
合成路线1
该中间体在本合成路线中的序号：(B)This compound can be prepared by two related ways: 1) The reaction of ethyl (2-hydroxypropyl)amine (A) with 3,6-dichloropyridazine (I) in refluxing toluene gives 3-chloro-6-[ethyl(2-hydroxypropyl)amino]pyridazine (II). This intermediate is then reacted with ethyl hydrazinecarboxylate (B) to afford (III). 2) Alternatively, compound (II) may be treated with hydrazine hydrate to afford the hydrazinopyridazine (IV); acylation of (IV) with ethoxycarbonyl chloride provides the final compound (III).
| 【1】 Pifferi, G.; Parravicini, F.; Scarpitta, G.; Dorigotti, L.; Derivati della 3-idrazinopiridazina. Nota III. Sintesi ed attivita antiipertensiva di nuove 3-(2-acilidrazino)piridazine-6-alchilamino sostituite. Farm Sci Ed 1979, 34, 299-310. |
| 【2】 Citero, L.; Visconti, M.; Borsa, M.; Pifferi, G.; Analytical profile of cadralazine, a new antihypttensive agent. Boll Chim Farm 1981, 120, 222-233. |
| 【3】 Carpi, C.; Dorigotti, L.; Pifferi, G. (ISF SpA); 6-Substituted 3-carbethoxyhydrazinopyridazines. US 4002753 . |
| 【4】 Meran, C.; Cadralazine. Drugs Fut 1982, 7, 6, 382. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 27366 | Ethyl hydrazinecarboxylate; Ethyl 1-hydrazinecarboxylate | 4114-31-2 | C3H8N2O2 | 详情 | 详情 |
| (A) | 31956 | Ethyl (2-hydroxypropyl)amine; 1-(Ethylamino)-2-propanol | 40171-86-6 | C5H13NO | 详情 | 详情 |
| (I) | 11292 | 3,6-Dichloropyridazine | 141-30-0 | C4H2Cl2N2 | 详情 | 详情 |
| (II) | 31957 | 3-Chloro-6-[ethyl(2-hydroxypropyl)amino]pyridazine; 1-[(6-Chloro-3-pyridazinyl)(ethyl)amino]-2-propanol | 64241-33-4 | C9H14ClN3O | 详情 | 详情 |
| (III) | 31958 | ethyl 2-[6-[ethyl(2-hydroxypropyl)amino]-3-pyridazinyl]-1-hydrazinecarboxylate | C12H21N5O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The cyctization of 4-chloro-2-(propylamino)aniline (I) with oxalyl chloride (II) in hot o-dichlorobenzene gives 1-propyl-7-chloroquinoxaline-2,3-dione (III), which by reaction with SOCl2 in DMF is converted to 3,7-dichloro-1-propyl-1H-quinoxalin-2-one (IV). The condensation of (IV) with ethyl carbazate (V) in refluxing acetonitrile affords ethyl 3-(7-chloro-1-propyl-2-oxo-1H-quinoxalin-3-yl)carbazate (VI), which is finally cyclized by heating at 260 C.
| 【1】 Brown, R.E.; Georgiev, V.; Kropp, P.; Loev, B. (USV Pharmaceutical Corp.); Triazaloquinoxalin-1,4-diones. EP 0039920; JP 57004988; US 4400382 . |
| 【2】 Chu, S.S.; Castaner, J.; Serradell, M.N.; RHC-3164. Drugs Fut 1985, 10, 12, 985. |
| 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) | 29840 | 4-chloro-N(2)-propyl-1,2-benzenediamine; N-(2-amino-5-chlorophenyl)-N-propylamine | C9H13ClN2 | 详情 | 详情 | |
| (II) | 29841 | Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride | 79-37-8 | C2Cl2O2 | 详情 | 详情 |
| (III) | 29842 | 7-chloro-1-propyl-1,4-dihydro-2,3-quinoxalinedione | C11H11ClN2O2 | 详情 | 详情 | |
| (IV) | 29843 | 3,7-dichloro-1-propyl-2(1H)-quinoxalinone | C11H10Cl2N2O | 详情 | 详情 | |
| (V) | 27366 | Ethyl hydrazinecarboxylate; Ethyl 1-hydrazinecarboxylate | 4114-31-2 | C3H8N2O2 | 详情 | 详情 |
| (VI) | 29844 | ethyl 2-(6-chloro-3-oxo-4-propyl-3,4-dihydro-2-quinoxalinyl)-1-hydrazinecarboxylate | C14H17ClN4O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)The reaction of 6,8-dinitro-2H-1,4-benzoxazine-3(4H)-thione (I) with ethyl carbazate (II) in refluxing ethanol gives 6,8-dinitro-3-(2-ethoxy-carbonyl)hydrazino-2H-1,4-benzoxazine (III), which undergoes ring closure in refluxing o-dichlorobenzene to give the title compound.
| 【1】 Shridhar, D.R.; Potential diuretics. Part I. Synthesis of some substituted 2,4-dihydro-1-oxo/thioxo-1,2,4-triazolo[3,4-c][1,4]benzoxazines - Novel diuretic agents. Indian J Chem 1984, 238, 1279. |
| 【2】 Shridhar, D.R.; Arya, V.P.; IDPH-8032. Drugs Fut 1985, 10, 7, 559. |
合成路线4
该中间体在本合成路线中的序号：(II)The cyclocondensation of 2H-1,4 benzoxazine-3(4H)-thione (IV) with ethyl carbazate (II) in refluxing DMF gives 2,4-dihydro[1,2,4]triazolo[3,4-c][1,4]benzoxazin-1-one (V), which is nitrated at room temperature with a mixture of concentrated HNO3 and H2SO4.
| 【1】 Shridhar, D.R.; Potential diuretics. Part I. Synthesis of some substituted 2,4-dihydro-1-oxo/thioxo-1,2,4-triazolo[3,4-c][1,4]benzoxazines - Novel diuretic agents. Indian J Chem 1984, 238, 1279. |
| 【2】 Shridhar, D.R.; Arya, V.P.; IDPH-8032. Drugs Fut 1985, 10, 7, 559. |