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Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 578-46-1 * Storage: {[proInfo.prStorage]}
* 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 indium; indium(III) chloride In methanol for 2.33333 h; Reflux; Inert atmosphere
General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10percent NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87percent. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10percent ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).
Reference：
[1] Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170
3
[ 578-46-1 ]
[ 38939-88-7 ]
Reference：
[1] Journal of the Chemical Society, 1929, p. 2742
4
[ 537-92-8 ]
[ 611-05-2 ]
[ 578-46-1 ]
Reference：
[1] Journal of the Chemical Society, 1949, p. 1624
[2] Journal of the Society of Chemical Industry, London, 1939, vol. 58, p. 152
[3] Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170
[4] Journal of the Society of Chemical Industry, London, 1939, vol. 58, p. 152
[5] Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170
5
[ 601-87-6 ]
[ 611-05-2 ]
[ 578-46-1 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1767 - 1772
6
[ 578-46-1 ]
[ 40385-54-4 ]
Reference：
[1] Journal of the Chemical Society, 1929, p. 2742
[2] Journal of the Chemical Society, 1926, p. 3221
[3] Journal of Organic Chemistry, 1961, vol. 26, p. 2805 - 2809
7
[ 578-46-1 ]
[ 446-34-4 ]
Reference：
[1] Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2376 - 2377
8
[ 610-39-9 ]
[ 578-46-1 ]
Reference：
[1] Journal of Organic Chemistry, 1980, vol. 45, # 24, p. 4992 - 4993
[2] Tetrahedron Letters, 1994, vol. 35, # 49, p. 9217 - 9220
Reference：
[1] Journal of the Chemical Society, 1949, p. 1624
[2] Journal of the Society of Chemical Industry, London, 1939, vol. 58, p. 152
[3] Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170
[4] Journal of the Society of Chemical Industry, London, 1939, vol. 58, p. 152
[5] Journal of the American Chemical Society, 1942, vol. 64, p. 1167,1170
11
[ 610-39-9 ]
[ 578-46-1 ]
[ 89-62-3 ]
Reference：
[1] Journal of the Chemical Society, 1921, vol. 119, p. 1052
[2] Journal of the Chemical Society, 1929, p. 2742
[3] Journal of the Chemical Society, 1920, vol. 117, p. 856
12
[ 102871-93-2 ]
[ 578-46-1 ]
Reference：
[1] Journal of the Chemical Society, 1913, vol. 103, p. 897[2] Journal of the Chemical Society, 1917, vol. 111, p. 613
[3] Justus Liebigs Annalen der Chemie, 1890, vol. 259, p. 224
Reference：
[1] Chemische Berichte, 1891, vol. 24, p. 564
15
[ 537-92-8 ]
[ 578-46-1 ]
Reference：
[1] Justus Liebigs Annalen der Chemie, 1908, vol. 359, p. 76
[2] Journal of the Chemical Society, 1903, vol. 83, p. 331
[3] Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 647,658
16
[ 25917-89-9 ]
[ 578-46-1 ]
Reference：
[1] Journal of the Chemical Society, 1913, vol. 103, p. 1397
[2] Journal of the Chemical Society, 1913, vol. 103, p. 1397
To a suspension of sodium hydride (95%, 684 mg, 27.1 mmol) in DMF (50 mL) at 0 C. was added a solution of <strong>[578-46-1]5-methyl-2-nitro-aniline</strong> (4 g, 26.3 mmol) in DMF (40 mL). After stirring for 10 minutes, methyl, iodide (7.2 mL, 114.8 mmol) was added dropwise over 20 min. The reaction was stirred for 1 h at 0 C. and then at room temperature for 1 h. The reaction was diluted with water, stirred for 10 min, and compound 37 was obtained as a red solid and collected by vacuum filtration.
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