73568-27-1 2-氯-6-甲基喹啉-3-甲醛

运输方式：冰袋运输。危险性质：非危险化学品。WGK Germany:3。海关编码:2933.49.7000。危险等级：刺激性物质（眼部刺激类别2、经皮刺激类别2、特异性靶器官毒性-一次接触类别3）。存储类别：11 - 可燃固体。

化学合成。

化学合成

路线1：Vilsmeier-Haack反应

• 步骤: 在冰冷却下混合3.5ml DMF和17ml POCl₃，搅拌后加入2.24g（15mmol）化合物1，加热至90℃反应10小时，冷却后倒入500毫升冰水中，得到化合物2（2.7克，产率87％）。
• 条件: 90℃；10小时；冰水冷却
• 收率: 87%
• 参考文献: [1] Synlett, 2001, #2, p.251-253；[2] Patent: CN104774221, 2017, B；[3] Patent: CN104725431, 2017, B；[4] Synthetic Communications, 2002, vol.32, #9, p.1351-1356；[5] Journal of the Brazilian Chemical Society, 2014, vol.25, #2, p.365-371；[6] Patent: CN106831566, 2017, A；[7] Tetrahedron, 2009, vol.65, #34, p.7099-7104；[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol.44, #9, p.1868-1875；[9] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol.45, #1, p.292-296；[10] Asian Journal of Chemistry, 2015, vol.27, #10, p.3667-3670；[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p.1520-1530；[12] Tetrahedron Letters, 2006, vol.47, #44, p.7779-7782；[13] Medicinal Chemistry Research, 2012, vol.21, #9, p.2340-2348,9；[14] European Journal of Medicinal Chemistry, 2010, vol.45, #8, p.3384-3388；[15] Asian Journal of Chemistry, 2011, vol.23, #10, p.4511-4516；[16] Bioorganic and Medicinal Chemistry, 2011, vol.19, #1, p.77-90；[17] Synlett, 2000, #8, p.1115-1118；[18] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol.50, #10, p.1491-1495；[19] Synthetic Communications, 2016, vol.46, #3, p.287-291；[20] Patent: US2008/139558, 2008, A1；[21] Heterocyclic Communications, 2003, vol.9, #3, p.281-286；[22] Synthetic Communications, 2004, vol.34, #11, p.2019-2024；[23] Synlett, 2007, #12, p.1873-1876；[24] Synlett, 2006, #16, p.2593-2596；[25] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol.183, #8, p.1870-1883；[26] Chemical and Pharmaceutical Bulletin, 2009, vol.57, #6, p.557-560；[27] Journal of Organometallic Chemistry, 2010, vol.695, #7, p.1065-1068；[28] Chemical and Pharmaceutical Bulletin, 2010, vol.58, #3, p.301-306；[29] European Journal of Medicinal Chemistry, 2011, vol.46, #5, p.1897-1905；[30] Letters in Organic Chemistry, 2010, vol.7, #3, p.229-234；[31] Bioorganic and Medicinal Chemistry Letters, 2011, vol.21, #16, p.4919-4923；[32] Heterocyclic Communications, 2011, vol.17, #3-4, p.111-119；[33] Bioorganic and Medicinal Chemistry Letters, 2012, vol.22, #2, p.942-944；[34] Chinese Chemical Letters, 2012, vol.23, #3, p.273-276；[35] Journal of the Serbian Chemical Society, 2012, vol.77, #3, p.279-286；[36] Chinese Chemical Letters, 2012, vol.23, #4, p.454-457；[37] Journal of Chemical Sciences, 2011, vol.123, #5, p.645-655；[38] Bioorganic and Medicinal Chemistry Letters, 2012, vol.22, #11, p.3816-3821；[39] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol.51, #5, p.746-751；[40] Medicinal Chemistry Research, 2012, vol.21, #7, p.1188-1198；[41] Journal of Chemical Sciences, 2012, vol.124, #3, p.669-677；[42] European Journal of Medicinal Chemistry, 2012, vol.54, p.239-247；[43] Bioorganic and Medicinal Chemistry Letters, 2013, vol.23, #1, p.107-111；[44] Chinese Chemical Letters, 2012, vol.23, #12, p.1367-1370；[45] Indian Journal of Heterocyclic Chemistry, 2011, vol.21, #1, p.69-72；[46] Medicinal Chemistry, 2015, vol.11, #6, p.580-589；[47] Research on Chemical Intermediates, 2018, vol.44, #4, p.2439-2449；[48] Tetrahedron, 2013, vol.69, #41, p.8668-8674；[49] Letters in Organic Chemistry, 2013, vol.10, #2, p.94-99；[50] Medicinal Chemistry Research, 2014, vol.23, #1, p.402-407；[51] Chinese Chemical Letters, 2014, vol.25, #7, p.1073-1076；[52] RSC Advances, 2017, vol.7, #29, p.17923-17933；[53] Journal of Molecular Structure, 2014, vol.1070, #1, p.10-20；[54] Tetrahedron Letters, 2014, vol.55, #31, p.4395-4399；[55] European Journal of Medicinal Chemistry, 2014, vol.83, p.569-580；[56] Letters in Organic Chemistry, 2014, vol.11, #10, p.736-742；[57] Asian Journal of Chemistry, 2014, vol.26, #21, p.7449-7451；[58] Chemical Communications, 2015, vol.51, #44, p.9125-9128；[59] Journal of the Iranian Chemical Society, 2015, vol.12, #8, p.1313-1324；[60] Journal of the Iranian Chemical Society, 2015, vol.12, #9, p.1577-1584；[61] Journal of Agricultural and Food Chemistry, 2015, vol.63, #23, p.5587-5596；[62] Bioorganic and Medicinal Chemistry Letters, 2015, vol.25, #17, p.3601-3605；[63] Organic and Biomolecular Chemistry, 2015, vol.13, #30, p.8211-8220；[64] Research on Chemical Intermediates, 2015, vol.41, #8, p.5509-5519；[65] Medicinal Chemistry Research, 2015, vol.24, #11, p.3892-3911；[66] Bioorganic and Medicinal Chemistry Letters, 2016, vol.26, #9, p.2278-2283；[67] MedChemComm, 2016, vol.7, #9, p.1832-1848；[68] Bioorganic and Medicinal Chemistry Letters, 2016, vol.26, #7, p.1696-1703；[69] European Journal of Medicinal Chemistry, 2017, vol.141, p.567-583；[70] Bioorganic and Medicinal Chemistry Letters, 2018, vol.28, #13, p.2244-2249；[71] Journal of Heterocyclic Chemistry, 2017, vol.54, #1, p.102-109；[72] Journal of Heterocyclic Chemistry, 2017, vol.54, #5, p.2740-2747；[73] ACS Combinatorial Science, 2017, vol.19, #8, p.555-563；[74] European Journal of Medicinal Chemistry, 2018, vol.151, p.226-236；[75] Journal of Heterocyclic Chemistry, 2018, vol.55, #4, p.1002-1009

路线2：TCTA-DMFreagent法

• 步骤: 向制备的TCTA-DMFreagent中加入9.8mmol乙酰苯胺并在回流条件下搅拌，通过TLC检查反应进程直至完成，用水淬灭后萃取，柱色谱纯化（硅胶，乙酸乙酯/正己烷）；或在0℃下，将三氯化磷（237.2g，1.55mol）逐滴加入搅拌中的N,N-二甲基甲酰胺（40.4g，552.74mmol）中，加入N-对甲苯基乙酰胺（33g，221.19mmol），保持回流搅拌过夜，用H₂O/冰混合物淬灭，调节pH至9，二氯甲烷萃取，无水MgSO₄干燥，旋转蒸发浓缩，硅胶柱色谱纯化（洗脱剂1:10乙酸乙酯:己烷）。
• 条件: 回流；过夜；0℃；TLC监测；硅胶柱色谱（乙酸乙酯/正己烷）
• 收率: 87%
• 参考文献: [1] Tetrahedron Letters, 2015, vol.56, #37, p.5164-5167；[1] Synlett, 2001, #2, p.251-253；[4] Synthetic Communications, 2002, vol.32, #9, p.1351-1356；[5] Journal of the Brazilian Chemical Society, 2014, vol.25, #2, p.365-371