1-(2-hydroxy-5-nitrophenyl)-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】50842

【品名】1-(2-hydroxy-5-nitrophenyl)-1-ethanone

【CA登记号】

【分子式】C₈H₇NO₄

【分子量】181.14792

【元素组成】C 53.04% H 3.89% N 7.73% O 35.33%

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)

The reaction of 4-nitrophenol (I) with acetic anhydride in aqueous NaOH gives the corresponding acetate (II), which is submitted to a Fries migration with AlCl3 in nitrobenzene at 140 C to yield the acetophenone (III). The condensation of (III) with epichlorohydrin (IV) by means of K2CO3 affords the adduct (V), which is treated with tert-butylamine (VI) in water to obtain the aminoisopropanol derivative (VII). The reduction of the nitro group of (VII) with H2 over Pd/C in methanol gives the corresponding amino derivative (VIII), which is finally condensed with N,N-diethylcarbamoyl chloride (IX) by means of TEA in THF to yield the target urea.

参考文献中间体

合成目标

【1】 Joshi, R.A.; et al.; A new and improved process for celiprolol hydrochloride. Org Process Res Dev 2001, 5, 2, 176.

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)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(II)	50841	4-Nitrophenyl acetate; Acetic acid 4-nitrophenyl ester; p-Nitrophenyl acetate	830-03-5	C₈H₇NO₄	详情	详情
(III)	50842	1-(2-hydroxy-5-nitrophenyl)-1-ethanone		C₈H₇NO₄	详情	详情
(IV)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(V)	50843	1-[5-nitro-2-(2-oxiranylmethoxy)phenyl]-1-ethanone		C₁₁H₁₁NO₅	详情	详情
(VI)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情
(VII)	50844	1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-nitrophenyl]-1-ethanone		C₁₅H₂₂N₂O₅	详情	详情
(VIII)	33819	1-[5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1-ethanone		C₁₅H₂₄N₂O₃	详情	详情
(IX)	33816	N,N'-Diethylcarbamoyl chloride; 1-[(chlorocarbonyl)(ethyl)amino]ethane	88-10-8	C₅H₁₀ClNO	详情	详情

Extended Information