3-nitrobenzoyl chloride; m-nitrobenzoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】15293

【品名】3-nitrobenzoyl chloride; m-nitrobenzoyl chloride

【CA登记号】121-90-4

【分子式】C₇H₄ClNO₃

【分子量】185.5664

【元素组成】C 45.31% H 2.17% Cl 19.11% N 7.55% O 25.87%

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：(V)

Several procedures for obtaining titte compound have been reported: In one method the acylation of 1 naphthylamine 4,6,8-trisulfonic acid trisodium salt (I) with 4 methyl-3-nitrobenzoyt chloride (II) yields the correspond ing amide (III), which is reduced with Fe in acetic acid to the amine (IV). Acylation of (IV) with 3-nitrobenzoyl chloride (V) affords the nitro diamide (VI), which is reduced with Fe and acetic acid before to the amine (VII). Finally, this compound is condensed with phosgene.

参考文献中间体

合成目标

【1】 Heymann; Angew Chem 1924, 37, 585.
【2】 Freres, P.; Foruneau, E.; Trefouel, J.; The manufacture of a symmetrical urea of m-aminobenzoyl-m-aminomethylbenzoyl-1-napthylamino-4,6,8-trisulphonate of sodium. GB 224849 .
【3】 Fourneau; et al.; Compt Rend Acad Sci 1924, 178, 675.
【4】 Castaner, J.; Serradell, M.N.; Suramin Sodium. Drugs Fut 1986, 11, 10, 860.

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)	23913	8-Aminonaphthalene-1,3,5-trisulfonic acid trisodium salt		C₁₀H₆NNa₃O₉S₃	详情	详情
(II)	23914	4-methyl-3-nitrobenzoyl chloride	10397-30-5	C₈H₆ClNO₃	详情	详情
(III)	23915	4-Methyl-3-nitro-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt		C₁₈H₁₁N₂Na₃O₁₂S₃	详情	详情
(IV)	23916	3-Amino-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt		C₁₈H₁₃N₂Na₃O₁₀S₃	详情	详情
(V)	15293	3-nitrobenzoyl chloride; m-nitrobenzoyl chloride	121-90-4	C₇H₄ClNO₃	详情	详情
(VI)	23918	4-Methyl-3-(3-nitrobenzamido)-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt		C₂₅H₁₆N₃Na₃O₁₃S₃	详情	详情
(VII)	23919	3-(3-Aminobenzamido)-4-methyl-N-(4,6,8-trisulfonaphthalen-1-yl)benzamide trisodium salt		C₂₅H₁₈N₃Na₃O₁₁S₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III), which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V). The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI), which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII). Finally, this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.

参考文献中间体

合成目标

【1】 Mealy, N.; Castaner, J.; FK-143. Drugs Fut 1996, 21, 5, 473.
【2】 Golden, P.; Hashimoto, M.; Tanaka, H.; Sawada, Y.; Okada, S.; Sawada, K.; Kayakiri, N.; 4-(1-Benzoylindol-3-yl)butyric acids and FK143: Novel nonsteroidal inhibitors of steroid 5alpha-reductase (II). Chem Pharm Bull 1999, 47, 4, 481.
【3】 Okada, S.; Sawada, K.; Kayakiri, N.; Saitoh, Y.; Tanaka, H.; Hashimoto, M. (Fujisawa Pharmaceutical Co., Ltd.); Indole derivs. EP 0458207; JP 1992244061; US 5212320; US 5312829 .

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)	15292	Indole; 1H-indole	120-72-9	C₈H₇N	详情	详情
(II)	15293	3-nitrobenzoyl chloride; m-nitrobenzoyl chloride	121-90-4	C₇H₄ClNO₃	详情	详情
(III)	15294	1H-indol-3-yl(3-nitrophenyl)methanone		C₁₅H₁₀N₂O₃	详情	详情
(IV)	11263	ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate	2969-81-5	C₆H₁₁BrO₂	详情	详情
(V)	15296	ethyl 4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butanoate		C₂₁H₂₀N₂O₅	详情	详情
(VI)	15297	4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butyric acid		C₁₉H₁₆N₂O₅	详情	详情
(VII)	15298	4-[3-(3-aminobenzoyl)-1H-indol-1-yl]butyric acid		C₁₉H₁₈N₂O₃	详情	详情
(VIII)	15299	1-[chloro(4-isobutylphenyl)methyl]-4-isobutylbenzene		C₂₁H₂₇Cl	详情	详情

Extended Information