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Synthesis of mono-substituted derivatives of 6-aminoquinoline 被引量：1

Synthesis of mono-substituted derivatives of 6-aminoquinoline
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摘要 Several 6-aminoquinoline derivatives,which could be used in drug design,have been synthesized.The reaction conditions were comparatively studied,and the p-chloroaniline was used as optimum oxidant in Skraup-Doebner-Von Miller reaction.The nitro group was reduced effectively by SnCl2 with no halo-removed occurred. Several 6-aminoquinoline derivatives,which could be used in drug design,have been synthesized.The reaction conditions were comparatively studied,and the p-chloroaniline was used as optimum oxidant in Skraup-Doebner-Von Miller reaction.The nitro group was reduced effectively by SnCl2 with no halo-removed occurred.
作者 Tian Lan Xian Xia Yuan Jiang Hong Yu Chao Jia Yu Shi Wang Hui Juan Zhang Zi Feng Ma Wei Dong Ye
机构地区 School of Chemistry and Chemical Engineering School of Pharmacy Xinchang Pharmaceutical Factory
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第3期253-255,共3页 中国化学快报（英文版）
基金 the financial support of this work by the National Science Foundation of China(No 20776085) the 973 Program of China(No2007CB209700) the STCSM of China(Nos10JC1406900 and 09XD1402400) the Foundation of Zhejiang Pharmaceutics CoLtd the Opening Foundation of Zhejiang Provincial Top Key Discipline
关键词 6-Aminoquinoline 6-Nitroquinoline Skraup reaction OXIDANT 6-Aminoquinoline 6-Nitroquinoline Skraup reaction Oxidant
分类号 TQ612.1 [化学工程—精细化工] O626.323 [理学—有机化学]
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  • 95- and 7-chloro-6-nitroquinolines: To stirred liquid of m-chloroaniline (20 mL) was added acetic anhydride dropwise at room temperature until all the starting material consumed. The resulted mixture was neutralized by aqueous ammonia, and the obtained solid was filtered, washed thoroughly with water. After vacuum drying, 28 g nearly pure rn-chloroacetanilide was obtained. To a well-stirred mixture of rn- chloroaeetanilide (18 g) and concentrated sulfuric acid (180 mL) was slowly added guanidinium nitrate (16 g) while maintaining the temperature at 5-10 ~C. After the addition completed, the reaction mixture was poured into ice water (800 mL), and the solid obtained was filtered, washed with water and dried in vacuum oven for 8 h, a yellow product weighted 22 g was obtained, which was then purified through recrystallization to get 3-chloro-4-nitroacetanilide. A mixture of 3-chloro-4-nitroacetanilide (1.0 g), water (3.0 mL), concentrated sulfuric acid (4.0 mL), glycerol (2.5 mL), and p-chloroaniline (1.5 g) was boiled gently under reflux for 3 h. The product was cooled, diluted to 50 mL and filtered, the residue was disposed and the filtrate was adjusted to alkaline with aqueous ammonia. The precipitate was filtered off, washed and dried. Purification of the product by column chromatography gave the corresponding products. 5-Chloro-6-nitroquinohnes: ~H NMR (400 MHz, DMSO-da): 8 9.14 (dd, 1H, J = 4.4, 1.6 Hz), 8.75 (d, 1H, J = 8.8 Hz), 8.28 (d, 1H, J= 8.8 Hz), 8.19 (d, 1H, J = 8.8 Hz), 7.84 (dd, 1H, J = 8.8, 4.4 Hz), 35%. 7-Chloro-6-nitroquinolines: 1H NMR (400 MHz, DMSO-d6): 8 9.09 (dd, 1H, J = 4.4, 1.6 Hz), 8.87 (s, 1H), 8.58 (d, 1H, J = 8.8 Hz), 8.33 (s, 1H), 7.72 (dd, 1H, J = 8.8, 4.4 Hz), 27%.
  • 10General procedure for 6-aminoquinolines: The 6-nitroquinoline derivative (0.1 g) was added slowly with stirring to 1.0 g stannous chloride in 5 mL of 6 mol/L hydrochloric acid with gently heating for 1 h. After neutralizing the reaction mixture by aqueous ammonia, the precipitate was extracted with CH2C12 (4 x 20 mL). The combined CH2C12 layer was dried with anhydrous MgSO4. Evaporating and chromatographing the extraction gave corresponding pure 6-aminoquinoline. 2-chloro-6-aminoquinoline: 1H NMR (400 MHz, DMSO-d6): & 8.99 (d, 1H, J = 8.4 Hz), 7.61 (d, 1H, J = 8.8 Hz), 7.27 (d, 1H, J = 8.4 Hz), 7.17 (dd, 1H, J = 8.8, 2.8 Hz), 7.03 (d, 1H, J = 2.8 Hz), 5.71 (s, 2H); Anal. Calcd. for C9HTN2CI: C, 60.33; H, 3.91; N, 15.64. Found: C, 60.56; H, 3.74; N, 15.31.

同被引文献11

  • 1刘博,周文,叶健,徐方方,绍颖然,李金维,张绪得.6-氨基喹啉合成研究[J].精细化工中间体,2012,42(6):28-30. 被引量：2
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  • 3LIU X W, LI J, LI H, et al. Synthesis, characteriza- tion, DNA-binding and photocleavage of complexes [Ru(phen)2(6-OH-dppz) ]2 and [Ru(phen)2(6-NO- 2-dppz) ][J]. Journal of Inorganic Biochemistry, 2005, 99(12) : 2372-2380.
  • 4ZHENG S L, ZHANG J P, WONG W T, et al. A nov- el highly electrical conducting single-component molecular material: [Aga (Hophen)2 (Hophen =IH- [ 1,10]phenanthrolin-2-one) [J]. Journal of the Amer- ican Chemical Society, 2003, 125(23) :6882-6883.
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  • 6BARTON J K, BASILE L A, DANISHEFSKY A, et al. Chiral probes for the handedness of DNA helices: enantiomers of tris (4,7-diphenylphenanthroline) ruthenium (11)[J]. Proceedings of the National Acade- my of Sciences, 1984, 81(7): 1961-1965.
  • 7BARTON J K, LOLIS E. Chiral discrimination in thecovalent binding of bis (phenanthroline) dichlororu -the- nium (11) to B-DNA [J]. Journal of the American Chemical Society, 1985, 107 : 708 - 709.
  • 8MORERA C, PALOMEPO E G. Triple substi tuted phenanthroline derivatives for the treatment of neurode- generative or heamatologicaldiseases or conditions:EP, 2196466A1 [P]. 2008-12-10.
  • 9PIPLANI P, RAANI A, SANDHIR R. Synthesis and pharmaeolegieal evaluation of some quinoline deriva- tives as potential antiamnesic agents [J]. Journal of Young Pharmacists, 2009( 1 ) : 341-350.
  • 10WIELGOSZCOLLIN G,DUFLOSN M. 8-Amino-5-ni- tro-6-phenoxyquinolines: Potential Non-peptidic neu- ropeptide Y receptor ligands [ J ]. Journal of Enzyme Inhibition and Medicinal Chemistry, 2002,17 (6) : 449- 453.

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Chinese Chemical Letters
2011年 第3期

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