2-Chloro-5-nitrobenzoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】10189

【品名】2-Chloro-5-nitrobenzoyl chloride

【CA登记号】25784-91-2

【分子式】C₇H₃Cl₂NO₃

【分子量】220.01116

【元素组成】C 38.21% H 1.37% Cl 32.23% N 6.37% O 21.82%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(II)

A more complete synthesis for LF-1695 has been reported: The reaction of 2-chloro-5-nitrobenzoic acid (I) with PCl5 in hot chlorobenzene gives the corresponding acyl chloride (II), which is condensed with chlorobenzene (III) by means of AlCl3, yielding 2,4'-dichloro-5-nitrobenzophenone (IV). The condensation of (IV) with 4-methylpiperidine (V) by means of K2CO3 at 150 C affords 4'-chloro-2-(4-methylpiperidin-1-yl)-5-nitrobenzophenone (VI), which is finally reduced with Fe or SnCl2 and HCl.

参考文献中间体

合成目标

【1】 Ou, K.; Robin, J.; Bellamy, F.D.; Dodey, P.; Chazan, J.B.; Pascal, M.; Dutartre, P.; (Benzoylphenyl)piperidines: A new class of immunomodulators. J Med Chem 1991, 34, 5, 1545-52.

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)	10188	2-Chloro-5-nitrobenzoic acid	2516-96-3	C₇H₄ClNO₄	详情	详情
(II)	10189	2-Chloro-5-nitrobenzoyl chloride	25784-91-2	C₇H₃Cl₂NO₃	详情	详情
(III)	10190	1-Chlorobenzene	108-90-7	C₆H₅Cl	详情	详情
(IV)	10191	(2-Chloro-5-nitrophenyl)(4-chlorophenyl)methanone		C₁₃H₇Cl₂NO₃	详情	详情
(V)	10192	4-Methylpiperidine; gamma-Pipecoline	626-58-4	C₆H₁₃N	详情	详情
(VI)	10193	(4-Chlorophenyl)[2-(4-methylpiperidino)-5-nitrophenyl]methanone		C₁₉H₁₉ClN₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The title carboxamide is prepared by coupling 2-chloro-5-nitrobenzoyl chloride (I) with 4-aminopyridine (II) in DMA

参考文献中间体

合成目标

【1】 Amemiya, Y.; Wakabayashi, K.; Takaishi, S.; Fukuda, C. (Sankyo Co., Ltd.); PPARgamma modulators. EP 1277729; JP 2002332266; WO 0183427 .

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)	10189	2-Chloro-5-nitrobenzoyl chloride	25784-91-2	C₇H₃Cl₂NO₃	详情	详情
(II)	25661	4-pyridinamine; 4-aminopyridine	5044-74-5	C₅H₆N₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

Treatment of 2-chloro-5-nitrobenzoic acid (I) with PCl5 provides acid chloride (II), which is then condensed with anisole in the presence of AlCl3 to furnish the benzophenone (III). Alternatively, ketone (III) is prepared by Friedel-Crafts condensation of 2-chloro-5-nitrobenzoic acid (I) with anisole in hot polyphosphoric acid. Reduction of ketone (III) employing triethylsilane and trifluoromethanesulfonic acid gives rise to diphenylmethane derivative (IV)

参考文献中间体

合成目标

【1】 Manning, R.E.; Tremont, S.J.; Glenn, K.C.; Keller, B.T. (Pharmacia Corp.); Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders. WO 0168096 .

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)	10188	2-Chloro-5-nitrobenzoic acid	2516-96-3	C₇H₄ClNO₄	详情	详情
(II)	10189	2-Chloro-5-nitrobenzoyl chloride	25784-91-2	C₇H₃Cl₂NO₃	详情	详情
(III)	59706	(2-chloro-5-nitrophenyl)(4-methoxyphenyl)methanone		C₁₄H₁₀ClNO₄	详情	详情
(IV)	59707	4-(2-chloro-5-nitrobenzyl)phenyl methyl ether; 1-chloro-2-(4-methoxybenzyl)-4-nitrobenzene		C₁₄H₁₂ClNO₃	详情	详情

Extended Information