2-(2-methyl-3-nitrophenyl)-N,N-dipropylacetamide -Drug Synthesis Database

【结构式】

【分子编号】34862

【品名】2-(2-methyl-3-nitrophenyl)-N,N-dipropylacetamide

【CA登记号】

【分子式】C₁₅H₂₂N₂O₃

【分子量】278.35136

【元素组成】C 64.73% H 7.97% N 10.06% O 17.24%

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 condensation of 2-(2-methyl-3-nitrophenyl)acetic acid (I) with dipropylamine (II) by means of refluxing SOCl2 gives the corresponding amide (III), which is reduced with borane/THF yielding the tertiary amine (IV). The condensation of (IV) with diethyl oxalate by means of sodium ethoxide in refluxing ethanol affords the pyruvate ester (V), which is treated with NaOH and H2O2 yielding the acetic acid derivative (VI). Finally, this compound is cyclyzed by hydrogenation with H2 over Pd/C in ethanol.

参考文献中间体

合成目标

【1】 Gallagher, G. Jr. (SmithKline Beecham Corp.); 4-Aminoalkyl-2(3H)-indolones. EP 0113964; ES 8600239; ES 8604143; US 4452808 .

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)	34861	2-(2-methyl-3-nitrophenyl)acetic acid		C₉H₉NO₄	详情	详情
(II)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情
(III)	34862	2-(2-methyl-3-nitrophenyl)-N,N-dipropylacetamide		C₁₅H₂₂N₂O₃	详情	详情
(IV)	34863	N-(2-methyl-3-nitrophenethyl)-N,N-dipropylamine; N-(2-methyl-3-nitrophenethyl)-N-propyl-1-propanamine		C₁₅H₂₄N₂O₂	详情	详情
(V)	17571	Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate	95-92-1	C₆H₁₀O₄	详情	详情
(VI)	34864	ethyl 3-[2-[2-(dipropylamino)ethyl]-6-nitrophenyl]-2-oxopropanoate		C₁₉H₂₈N₂O₅	详情	详情
(VII)	34865	2-[2-[2-(dipropylamino)ethyl]-6-nitrophenyl]acetic acid		C₁₆H₂₄N₂O₄	详情	详情

Extended Information