* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With ammonium hydroxide; ammonium cerium (IV) nitrate; hydroxylamine hydrochloride In water at 0℃;
A suspension of 2-chloroquinoline-3-carbaldehyde (0.01 mol) in30percent aqueous ammonia (30 mL) was stirred for 5 min at room temperature,resulting in formation of a turbid solution. To this, cericammonium nitrate (0.01 mol) was added with constant stirring at0 C. After completion of the reaction (monitored by TLC, 10–15 min), the mixture was extracted with chloroform–ethyl acetate(5:3), dried with anhydrous sodium sulfate, and concentrated underreduced pressure to give a crude product, which was crystalized inethanol to give pure 2-chloroquinoline-3-carbonitrile as pale yellowcrystals. Yield: 82percent.
58%
With pyridine; ammonium peroxydisulfate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 0.5℃; for 24 h; Molecular sieve; Sealed tube; Irradiation
General procedure: To an oven-dried 2 ml reaction vial equipped with a stir bar wasadded the aldehyde 3a (0.136 g, 1 mmol, 1 equiv) and pyridine(0.474 g, 6.0 mmol, 6 equiv), followed by acetonitrile (2 ml, 0.5M in 3a). The vial was then charged with Ru(bpy)3(PF6)2 (0.017g, 0.02 mmol, 0.02 equiv), 2 (0.043 g, 0.20 mmol, 0.20 equiv),(NH4)2S2O8(0.501 g, 2.2 mmol, 2.2 equiv), and activated 3 Åmolecular sieves (ca. 0.2 g), sealed with a cap, and irradiated inblue LED reactor for 24 h. In the absence of fan cooling, the temperatureof the reaction mixture plateaued at approximately 50°C . After the irradiation was complete, the reaction mixturewas quenched with EtOAc and transferred to a separatoryfunnel. Further EtOAc (30 ml) was added, followed by 0.5 MHCl(aq) (30 ml). The layers were separated, and the aqueous layerwas extracted with EtOAc (3 × 20 ml). The organic layers werethen combined and washed with 0.5 M 0.5 M HCl(aq) (2 × 20 ml),saturated aqueous sodium bicarbonate (2 × 20 ml), and finallybrine (20 ml). The organic layer was then dried over sodiumsulfate and the solvent removed in vacuo to afford the crudeproduct. The resulting crude mixture was adhered to silica gelusing 1.5 weight equivalents of SiO2(relative to the theoreticalyield). The dry-packed material was gently added on top of asilica gel plug. The plug was washed with an excess of hexanes(ca. 5 column volumes). The desired product was eluted off theplug via a 90:10 by volume mixture of hexanes/EtOAc (3–4column volumes). The solvent was removed in vacuo by rotaryevaporation affording the pure nitrile 3c (0.066 g, 50percent) as awhite solid.
Reference：
[1] Synlett, 2009, # 20, p. 3378 - 3382
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 292 - 296
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 1, p. 152 - 154
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 3, p. 602 - 611
[6] Synlett, 2018, vol. 29, # 16, p. 2185 - 2190
[7] Journal of Chemical Research - Part S, 2000, # 1, p. 30 - 31
[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[9] Archiv der Pharmazie, 2001, vol. 334, # 4, p. 117 - 120
[10] Patent: US4496569, 1985, A,
[11] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1202 - 1205
[12] Tetrahedron, 2011, vol. 67, # 47, p. 9219 - 9224
[13] Indian Journal of Heterocyclic Chemistry, 2012, vol. 21, # 3, p. 237 - 244
[14] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 894 - 909
[15] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 13, p. 2244 - 2249
2
[ 36926-82-6 ]
[ 95104-21-5 ]
Reference：
[1] Archiv der Pharmazie, 2001, vol. 334, # 4, p. 117 - 120
[2] Patent: US4496569, 1985, A,
3
[ 93299-49-1 ]
[ 95104-21-5 ]
Reference：
[1] Indian Journal of Heterocyclic Chemistry, 2012, vol. 21, # 3, p. 237 - 244
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
4
[ 103-84-4 ]
[ 95104-21-5 ]
Reference：
[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 292 - 296
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 3, p. 602 - 611
[5] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 13, p. 2244 - 2249
5
[ 91301-03-0 ]
[ 95104-21-5 ]
Reference：
[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
[3] Archiv der Pharmazie, 2001, vol. 334, # 4, p. 117 - 120
With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 2h;
General procedure: 2-chloro-6-substitutedquinoline-3-carbonitrile (2a-b) (1 mmol), morpholine (1 mmol) and anhydrous potassium carbonate (2 mmol) in dimethylformamide (10 mL) were charged in a 100 mL round bottom flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 90 C for 2 h. The progress of the reaction was monitored by TLC. After the completion of reaction as confirmed by TLC, the mixture was poured in to 100 mL ice-water to get solid product. The product was filtered, washed thoroughly with water, dried and recrystallized from ethanol to afford compounds (3a-b). 4.1.2.1. 2-Morpholinoquinoline-3-carbonitrile (3a). Yield: 78%; mp175-177 C; IR (KBr, numax, cm-1): 1211 (C-O-C); 1624 and 1592(C]N and C]C); 3051 (Ar, eCH str.); 1H NMR (CDCl3) delta ppm: 3.72(t, 4H, eCH2eNeCH2e), 3.93 (t, 4H, eCH2eOeCH2e), 7.40e8.40 (m,5H, AreH); ESI-MS (m/z): 240.1 (M+); Anal. Calcd for C14H13N3O: C,70.28; H, 5.48; N, 17.56; Found: C, 70.06; H, 5.22; N, 17.32.
General procedure: A mixture of 3a-3f (1.59 g, 7.3 mmol) and thiourea (1.11 g,14.6 mmol) in 20 mL of ethanol was refluxed for 1 h. After cooled toroom temperature, water (50 mL) was added and the mixture wasstirred for another 30 min. The product was yielded by filtration. 1HNMR and 13C NMR data of selected products are shown as follows.
2-Chloroquinoline-3-carbonitrile 2 (1.88 g, 0.01 mol) wasrefluxed with hydrazine hydrate (25 mL) for 5 h. The reaction mixturewas cooled, poured into water, and the resulting precipitatewas filtered off and crystallized from ethanol to give reddish orangecrystals. Yield: 76%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
