5-amino-2-hydroxy-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】38148

【品名】5-amino-2-hydroxy-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₈H₆N₂O₃

【分子量】178.14732

【元素组成】C 53.94% H 3.39% N 15.72% O 26.94%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

Condensation of 4-nitrophthalic anhydride (I) with O-benzyl hydroxylamine in refluxing toluene produced phthalimide (II). Catalytic transfer hydrogenation employing cyclohexene in the presence of Pd/C yielded 4-amino-N-hydroxyphthalimide (III), which was condensed with ethanesulfonyl chloride to give sulfonate (IV). Finally, acylation with acid chloride (V) furnished the title compound.

参考文献中间体

合成目标

【1】 Kerrigan, J.E.; et al.; 6-Acylamino-2-[(alkylsulfonyl)oxy]-1H-isoindole-1,3-dione mechanism-based inhibitors of human leukocyte elastase. Bioorg Med Chem Lett 2000, 10, 1, 27.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	14640	O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene	622-33-3	C₇H₉NO	详情	详情
(I)	31028	5-nitro-2-benzofuran-1,3-dione	5466-84-2	C₈H₃NO₅	详情	详情
(II)	38147	2-(benzyloxy)-5-nitro-1H-isoindole-1,3(2H)-dione		C₁₅H₁₀N₂O₅	详情	详情
(III)	38148	5-amino-2-hydroxy-1H-isoindole-1,3(2H)-dione		C₈H₆N₂O₃	详情	详情
(IV)	38149	5-amino-2-[(ethylsulfonyl)oxy]-1H-isoindole-1,3(2H)-dione		C₁₀H₁₀N₂O₅S	详情	详情
(V)	20650	methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate	1501-26-4	C₆H₉ClO₃	详情	详情

Extended Information