Metanitrophenol; 3-nitrophenol -Drug Synthesis Database

【结构式】

【分子编号】18076

【品名】Metanitrophenol; 3-nitrophenol

【CA登记号】554-84-7

【分子式】C₆H₅NO₃

【分子量】139.11064

【元素组成】C 51.8% H 3.62% N 10.07% O 34.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The reaction of 2-(chloromethyl)quinoline (I) with 3-nitrophenol (II) by means of Cs2CO3 in refluxing acetone gives the 3-nitrophenyl ether (III), which is reduced with H2 over Raney-Ni in ethanol to afford the 3-aminophenyl ether (IV). Finally this compound is sulfonated with trifluoromethanesulfonic anhydride and Et3N in dichloromethane.

参考文献中间体

合成目标

【1】 Kreft, A.; Musser, J.; Substituted-[2-quinolynil(bridged)aryl] compounds: modulators of eicosanoid biosynthesis and action. Drugs Fut 1990, 15, 1, 73.

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)	13162	2-(Chloromethyl)quinoline; alpha-Chloroquinaldine	4377-41-7	C₁₀H₈ClN	详情	详情
(II)	18076	Metanitrophenol; 3-nitrophenol	554-84-7	C₆H₅NO₃	详情	详情
(III)	43199	3-nitrophenyl 2-quinolinylmethyl ether; 2-[(3-nitrophenoxy)methyl]quinoline		C₁₆H₁₂N₂O₃	详情	详情
(IV)	31234	3-(2-quinolinylmethoxy)aniline; 3-(2-quinolinylmethoxy)phenylamine		C₁₆H₁₄N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Alkylation of 3-nitrophenol (I) with methyl bromoacetate (II) in the presence of K2CO3 provided phenoxyacetate (III). Then, reduction of the nitro group of (III) by hydrogenation on Pd/C gave amine (IV), which was subsequently condensed with N-tert-butoxycarbonyl glycine (V) on treatment with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) to afford amide (VI). Alkylation with bromoacetamide (VII) in the presence of NaH in THF provided (VIII), and removal of the Boc protecting group with trifluoroacetic acid gave amine (IX). This amine was condensed with 3-tolyl isocyanate (X) to give urea (XI). Then, alkaline hydrolysis of the ester group afforded acid (XII), which was finally condensed with N-methylaniline (XIII) to yield the target compound.

参考文献中间体

合成目标

【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 .
【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 .

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)	18076	Metanitrophenol; 3-nitrophenol	554-84-7	C₆H₅NO₃	详情	详情
(II)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(III)	18077	methyl 2-(3-nitrophenoxy)acetate		C₉H₉NO₅	详情	详情
(IV)	18078	methyl 2-(3-aminophenoxy)acetate		C₉H₁₁NO₃	详情	详情
(V)	18066	N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid	4530-20-5	C₇H₁₃NO₄	详情	详情
(V)	18068	2-bromo-N-methyl-N-phenylacetamide		C₉H₁₀BrNO	详情	详情
(VI)	18079	methyl 2-[3-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)phenoxy]acetate		C₁₆H₂₂N₂O₆	详情	详情
(VIII)	18080	methyl 2-(3-[[2-[(tert-butoxycarbonyl)amino]acetyl][2-(methylanilino)-2-oxoethyl]amino]phenoxy)acetate		C₂₅H₃₁N₃O₇	详情	详情
(IX)	18081	methyl 2-(3-[(2-aminoacetyl)[2-(methylanilino)-2-oxoethyl]amino]phenoxy)acetate		C₂₀H₂₃N₃O₅	详情	详情
(X)	18071	m-Tolyl Isocyanate; 1-isocyanato-3-methylbenzene; 3-methylphenyl isocyanate	621-29-4	C₈H₇NO	详情	详情
(XI)	18082	methyl 2-[3-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetate		C₂₈H₃₀N₄O₆	详情	详情
(XII)	18083	2-[3-([2-(methylanilino)-2-oxoethyl][2-[(3-toluidinocarbonyl)amino]acetyl]amino)phenoxy]acetic acid		C₂₇H₂₈N₄O₆	详情	详情
(XIII)	10409	N-Methyl-N-phenylamine; N-methylaniline; Monomethylaniline	100-61-8	C₇H₉N	详情	详情

Extended Information