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CAS No. :496-72-0 MDL No. :MFCD00007728
Formula : C7H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DGRGLKZMKWPMOH-UHFFFAOYSA-N
M.W : 122.17 Pubchem ID :10332
Synonyms :

Safety of [ 496-72-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 496-72-0 ]

* 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.

  • Upstream synthesis route of [ 496-72-0 ]
  • Downstream synthetic route of [ 496-72-0 ]

[ 496-72-0 ] Synthesis Path-Upstream   1~29

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YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In water for 3 h; Reflux (5-Methyl-1H-benzimidazole-2-yl)-methanol 25 was prepared using the Phillips procedure [1], 4-Methyl-1,2-phenylenediamine (12.22 g; 0.1 mol) and glycolic acid (11.40 g; 0.15 mmol) in hydrochloric acid (50 ml, 5.5 M) were heated under reflux with for 3 h. The reaction mixture was cooled to room temperature and ammonia solution was added and the mixture cooled in ice until a bright brown precipitate formed. The resulting solid was recrystallised from aqueous ethanol to give (5-methyl-1H-benzimidazole-2-yl)-methanol as a pale creamy powdery solid Yield 100percent.
72% at 130℃; for 3 h; General procedure: To a mixture of 1a–1c (10 mmol) with glycolic acid (2.28 g, 30 mmol) was added concentrated H3PO4(20 mL). The reaction mixture was refluxed at 130°C for 3 h, then quenched with 20percent NaOH. The respective solid product was collected by filtration.
70% at 150℃; for 3 h; Step 1
The mixture of 4-methyl-benzene-1,2-diamine (500 mg, 4.10 mmol) and hydroxy-acetic acid (374 mg, 4.92 mmol) was heated to 150° C. with stirring for 3 hrs.
After cooled to room temperature, the reactant was purified by silica gel column (DCM/MeOH=30/1) to afford (5-methyl-1H-benzoimidazol-2-yl)-methanol (400 mg, yield: 70percent) as a yellow solid.
Reference: [1] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[3] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016
[4] Patent: US2018/44324, 2018, A1, . Location in patent: Paragraph 0614
[5] Chemische Berichte, 1912, vol. 45, p. 3495
[6] Journal of the American Chemical Society, 1957, vol. 79, p. 4391,4393
[7] Journal of the Chemical Society, 1950, p. 1600,1602
[8] Biochemische Zeitschrift, 1955, vol. 327, p. 422,447
[9] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936
[10] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 584 - 600
  • 2
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YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 60 - 75℃; for 1 h;
Stage #2: With sodium hydroxide In water
6-Methylquinoxaline; A solution of 3,4-diaminotoluene (Aldrich, 100 g, 0.82 mol) in 600 mL of hot water (temp. 70-75° C.) was added rapidly to a 60° C. slurry of glyoxal-sodium bisulfite adduct (Aldrich, 239.5 g, 0.9 mol, 1.1 eq) in 400 mL of water. The resulting dark-brown clear solution was heated at 60° C. for 1 hr, then 5 g (0.02 mol) of additional glyoxal adduct was added. The mixture was allowed to cool to r.t. and filtered through a paper filter. The filtrate was neutralized with 5 M aq. NaOH to pH 7.5-7.8 and then extracted with ether (4.x.400 mL). The extract was dried over Na2SO4 and concentrated on a rotary evaporator to afford 92 g of brown oil which was distilled in vacuum (bp. 100-102° C. at 10 mm Hg; Cavagnol, J. C.; Wiselogle, F. Y. J. Am. Chem. Soc. 1947, 69, 795; 86° C. at 1 mm Hg). Yield 89 g (75percent) as a pale-yellow oil.
Reference: [1] Patent: US2005/282820, 2005, A1, . Location in patent: Page/Page column 17-18
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 7, p. 803 - 810
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 795,796
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YieldReaction ConditionsOperation in experiment
86% at 140℃; for 24 h; A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 °C in a siliconebath that contains a magnetic stirrer and a temperature controller.
Reference: [1] Journal of Catalysis, 2012, vol. 292, p. 118 - 129
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YieldReaction ConditionsOperation in experiment
98% With 10 wtpercent sulfated polyborate In neat (no solvent) at 100℃; for 0.05 h; Green chemistry General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / α-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wtpercent). The reaction mixture was stirred at 100 °C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.
92% at 20℃; for 1 h; General procedure: A mixture of 1,2-diamine (1 mmol) and α-dicarbonyl compound (1 mmol) was intimately mixed with pre-activated KF-alumina (1:4) (0.5 g) (Basic; Grade: Brockmann 1, and activated by heating under vacuum at 150 °C until bubbling ceases and then cooled to room temperature under vacuum) and stirred solid mixture with a magnetic spin bar at room temperature for hours as indicated in refPreviewPlaceHolderTable 4. After the reaction was complete, the solid mixture washed with diethyl ether (3 .x. 10 mL) and the solid was filtered off. The filtrate was concentrated and passed through a short column of silica gel to afford the quinoxalines. The desired product was pure on TLC and characterized by spectral (1H and 13C NMR) data and compared to those reported.
81% at 60℃; for 1 h; EXAMPLE 1 Preparation of: (5Z)-5-(6-quinoxalinylmethylidene)-2-[(2,6-dichlorophenyl)amino]-1,3-thiazol-4(5H)-one sodium salt a) 6-Methylquinoxaline. A suspension of 3,4-diaminotoluene (50.0 g; 0.409 mol.) and glyoxal (40percent aq. soin.; 52.0 mL; 0.450 mol.) in water (150 mL) and CH3CN (20.0 mL) was heated to 60° C. for 1 h. Heating was then discontinued and brine (100 mL) was added. The solution was extracted with EtOAc (3.x.150 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification via distillation under reduced pressure (120° C., 10 torr) provided 6-methylquinoxaline (48.0 g, 81percent) as a clear, colorless oil. 1 H NMR (400 MHz, CDCl3) δ ppm 2.61 (s, 3H) 7.61 (dd, J=8.59, 1.77 Hz, 1H) 7.88 (s, 1H) 8.00 (d, J=8.59 Hz, 1H) 8.79 (dd, J=9.85, 1.77 Hz, 2H) MS(ES+) m/e 145 [M+H]+
81% at 60℃; for 1 h; A suspension of 3,4-diaminotoluene (50.0 g; 0.409 mol.) and glyoxal (40percent aq. soln.; 52.0 mL; 0.450 mol.) in water (150 mL) and CH3CN (20.0 mL) was heated to 60 0C for 1 h. Heating was then discontinued and brine (100 mL) was added. The solution was extracted with EtOAc (3 x 150 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification via distillation under reduced pressure (1200C, 10 torr) provided 6-methylquinoxaline (48.0 g, 81 percent) as a clear, colorless oil. 1 H NMR (400 MHz, CDCl3) δ ppm 2.61 (s, 3 H) 7.61 (dd, J=8.59, 1.77 Hz, 1 H) 7.88 (s, 1 H) 8.00 (d, J=8.59 Hz, 1 H) 8.79 (dd, J=9.85, 1.77 Hz, 2 H) MS(ES+) m/e 145 [M+H]+. A suspension of 6-methylquinoxaline (8.O g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1 ,4-dioxane (5.0 mL) was irradiated at 2000C for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH2CI2, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel,20-50percent ethyl acetate in hexanes) followed by crystallization from CH2CI2 provided quinoxaline-6-carbaldehyde (40.0 g, 91percent) as a white solid. 1H NMR EPO <DP n="114"/>(400 MHz, CDCI3) δ ppm 10.25 (s, 1 H) 8.95 (s, 2 H) 8.57 (d, J=1.3 Hz, 1 H) 8.24 (dd, J=8.6, 1.5 Hz, 1 H) 8.20 (d, J=8.6 Hz, 1 H). MS(ES+) m/e 159 [M+H]+.
81% at 60℃; for 1 h; A suspension of 3,4-diaminotoluene (50.0 g; 0.409 mol.) and glyoxal (40percent aq. soln.; 52.0 ml
0.450 mol.) in water (150 mL) andCH3CN (20.0 mL) was heated to 60 0C for 1 h. Heating was then discontinued and brine (100 mL) was added. The solution was extracted with EtOAc (3 x 150 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification via distillation under reduced pressure (120 0C, 10 torr) provided 6-methylquinoxaline (48.0 g, 81percent) as a clear, colorless oil. 1 H NMR (400 MHz, CDCI3) δ ppm 2.61 (s, 3 H) 7.61 (dd, J=8.59, 1.77 Hz, 1 H) 7.88 (s, 1 H) 8.00 (d, J=8.59 Hz, 1 H) 8.79 (dd, J=9.85, 1.77 Hz, 2 H) MS(ES+) m/e 145 [M+H]+.
25% for 16 h; Example 8
6-Methylquinoxaline:
A solution of 4-methyl-1,2-phenylenediamine (5.0 g, 41 mmol) in methanol (250 mL) was treated with a solution of 40percent aqueous glyoxal and stirred for 16 h.
The solvent was evaporated and the residue was distilled under vacuum (2 mm Hg, 85-88° C.) to leave a colorless oil (1.5 g, 25percent). LC/MS Method A, r.t.=1.02 mins., purity=99.5percent.
25% for 16 h; 6-Methyl-quinoxaline: A solution of 4-methyl-1,2-phenylenediamine (5.0 g, 41 mmol) in methanol (250 mL) was treated with a solution of 40percent aqueous glyoxal and stirred for 16 h. The solvent was evaporated and the residue was distilled under vacuum (2 mm Hg, 85-88° C.) to leave a colorless oil (1.5 g, 25percent). LC/MS (Method A): r.t.=1.02 min., purity=99.5percent.

Reference: [1] Journal of Chemical Sciences, 2017, vol. 129, # 2, p. 141 - 148
[2] Heteroatom Chemistry, 2012, vol. 23, # 5, p. 472 - 477
[3] Tetrahedron Letters, 2011, vol. 52, # 49, p. 6597 - 6602
[4] Chinese Chemical Letters, 2011, vol. 22, # 6, p. 753 - 756
[5] Patent: US2007/179144, 2007, A1, . Location in patent: Page/Page column 4
[6] Synthesis (Germany), 2013, vol. 45, # 11, p. 1546 - 1552
[7] Patent: WO2006/127458, 2006, A2, . Location in patent: Page/Page column 112
[8] Patent: WO2006/133381, 2006, A2, . Location in patent: Page/Page column 7
[9] Patent: US2006/264631, 2006, A1, . Location in patent: Page/Page column 37
[10] Patent: US2006/270848, 2006, A1, . Location in patent: Page/Page column 39
[11] Chemische Berichte, 1884, vol. 17, p. 320[12] Justus Liebigs Annalen der Chemie, 1887, vol. 237, p. 334
[13] Chemische Berichte, 17 Ref. &lt;1884&gt;, 573, vol. &lt;4&gt; 8, p. 220,221
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 357 - 364
[15] Russian Journal of General Chemistry, 1997, vol. 67, # 2, p. 285 - 294
[16] Justus Liebigs Annalen der Chemie, 1887, vol. 237, p. 339[17] Justus Liebigs Annalen der Chemie, 1896, vol. 292, p. 246
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YieldReaction ConditionsOperation in experiment
87% at 120℃; for 23 h; Inert atmosphere; Molecular sieve General procedure: A mixture of phenylenediamine (0.9 mmol), diol or aminoalcohol (4.5 mmol), CsOH.H2O (1.8 mmol), complex 3b and molecular sieves (0.3 g) in a reaction tube was flushed with oxygen gas. The reaction mixture was heated in a oil bath at 120 C for 23 h. After cooling, water and ethyl acetate were added. The organic extracts were separated, dried and concentrated. The desired product was purified by chromatography with CH2Cl2/EtOAc 10/1as eluent.
Reference: [1] Journal of Organometallic Chemistry, 2014, vol. 775, p. 94 - 100
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Reference: [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837
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Reference: [1] Green Chemistry, 2017, vol. 19, # 11, p. 2515 - 2519
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 37, p. 6902 - 6907
[3] Synthetic Communications, 2013, vol. 43, # 20, p. 2801 - 2808
[4] Chemische Berichte, 1876, vol. 9, p. 222
[5] Chemische Berichte, 1887, vol. 20, p. 3001
[6] Chemische Berichte, 1876, vol. 9, p. 222
[7] Chemische Berichte, 1887, vol. 20, p. 3001
[8] Chemische Berichte, 1876, vol. 9, p. 222
[9] Chemische Berichte, 1887, vol. 20, p. 3001
[10] Chemische Berichte, 1876, vol. 9, p. 222
[11] Chemische Berichte, 1887, vol. 20, p. 3001
[12] Journal of Chemical Research, Miniprint, 1983, # 2, p. 352 - 357
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YieldReaction ConditionsOperation in experiment
82% With thionyl chloride; trimethylamine In dichloromethane for 5 h; Reflux
(1)
To a 250 mL three-neck flask were added commercial 4-methylbenzene-1,2-diamine (3.75 g, 0.03 mol), 60 mL of CH2Cl2 and, trimethylamine (13.14 g, 0.13 mol).
The solution was stirred until total dissolution of the diamine.
Sulfurous dichloride (11.47 g, 0.10 mol) was added dropwise very slowly and the mixture refluxed for 5 h.
After quenching the reaction with 1 mol/L sodium hydroxide solution, the solvent was extracted three times with dichloromethane (30 mL) and removed by rotary evaporation.
The residue was purified by silica gel column chromatography using pure petroleum ether as eluant to collect a brown needle solid, yield 3.69 g (82percent).
Mp 33-34 °C; 1H NMR (CDCl3, 400 MHz, TMS): δ 7.88 (d, 1H, J=9 Hz), 7.76 (s, 1H), 7.43 (d, 1H, J=9 Hz), 2.55 (s, 3H); 13C NMR (CDCl3, 100 MHz, TMS): δ 155.31, 153.54, 139.94, 132.41, 120.66, 119.76, 21.91; EIMS [M+] Calcd 150.0252, Found 150.0251.
82% With thionyl chloride In dichloromethane for 5 h; Inert atmosphere; Reflux To a 250 mL three-neck flask were added commercial 4- methylbenzene-1,2-diamine (3.75 g, 0.03 mol), 60 mL of CH2Cl2 and, trimethylamine (13.14 g, 0.13 mol). The solution was stirred until total dissolution of the diamine Sulfurous dichloride (11.47 g, 0.10 mol) was added dropwise very slowly and the mixture refluxed for 5 h. After quenching the reaction with 1 mol/L sodium hydroxide solution, the solvent was extracted 3 times with dichloromethane (30 mL) and removed by rotary evaporation. The residue was purified by silica gel column chromatography using pure petroleum ether as eluant to collect a brown needle solid, yield 3.69 g (82percent). m.p. 33e34 C; 1 H NMR (CDCl3, 400 MHz, TMS): d 7.88 (d, 1H, J 9 Hz), 7.76 (s, 1H), 7.43 (d, 1H, J 9 Hz), 2.55 (s, 3H); 13C NMR (CDCl3, 100 MHz, TMS): d 155.31, 153.54, 139.94, 132.41, 120.66, 119.76, 21.91; EI-MS [M] Calcd. 150.0252, Found 150.0251.
33% With thionyl chloride; triethylamine In benzene at 0℃; for 3 h; Reflux Compound 22 (4.8 g, 0.04 mol) was dissolved in the solution of benzene (150 mL) and TEA (20 mL).
To this mixture was added thionyl chloride (30 mL) at 0 °C and heated to reflux for 3 h.
When cooled to room temperature, the mixture was washed with water (100 mL), saturated sodium bicarbonate solution (100 mL) and brine (100 mL), dried with MgSO4 to obtain the crude product, which was purified by column chromatography on silica gel, eluting with ethyl acetate/petroleum (1:8) to afford product 23 (2 g, 33percent) as colorless granular crystal. Mp: 32-33 °C (lit.
Reference: [1] Tetrahedron, 2016, vol. 72, # 9, p. 1244 - 1248
[2] Tetrahedron, 2017, vol. 73, # 19, p. 2824 - 2830
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 5, p. 668 - 677
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
[5] Chemische Berichte, 1889, vol. 22, p. 2897
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 2, p. 534
[7] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1967, vol. 3, p. 662 - 666[8] Khimiya Geterotsiklicheskikh Soedinenii, 1967, vol. 3, # 5, p. 839 - 844
[9] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633
[10] Journal of Organic Chemistry, 1962, vol. 27, p. 676 - 677
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Reference: [1] Patent: CN103539760, 2016, B, . Location in patent: Paragraph 0065-0067
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Reference: [1] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1570,1572; engl. Ausg. S. 1643, 1645
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Reference: [1] Journal of the Chemical Society, 1948, p. 1310,1312
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  • [ 17635-21-1 ]
YieldReaction ConditionsOperation in experiment
99% With mesoporous silica SBA-15 functionalized with Cu(II)-DiAmSar complex In neat (no solvent) at 100℃; for 0.0833333 h; General procedure: A round-bottomed flask equipped with a magnet and condenserwas charged with the desired 1,2-diamine (1.0 mmol),1,2-diketone (1.0 mmol), and catalyst (Cu(II)DiAmSar/SBA-15,0.005 g). The resulting mixture was heated at 100 °C for theappropriate time. The course of the reaction was monitoredusing TLC on silica gel. Finally, the reaction mixture was cooled,and the crude mixture was purified by column chromatographyor crystallization to get the desired product. Spectral and physicaldata for all heterocycles were compared with referencesamples and were in accord with previously reported data.
98% With 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium hydrogen sulfate immobilized on cellulose In water at 20℃; for 0.0166667 h; Green chemistry General procedure: A vial containing a solution of 1,2-diketone (1 mmol) ando-diamine (1 mmol) and Cell-[pmim]HSO4 (300 mg) in water (3 mL) was stirred at room temperature for the time as shown in Table 2. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added to the reaction mixture and the insoluble catalyst was separated by filtration. The organic medium was removed with a rotary evaporator under reduced pressure.The crude product was purified by recrystallization from EtOH/H2O or by flash chromatography using ethyl acetate/n-hexane as eluent.
98% With 10 wtpercent sulfated polyborate In neat (no solvent) at 100℃; for 0.05 h; Green chemistry General procedure: To a mixture of substituted o-phenylenediamines derivative(2.0 mmol) and 1,2-diketone / α-hydroxy ketone (2.0 mmol),was added sulfated polyborate (10 wtpercent). The reaction mixture was stirred at 100 °C in an oil bath. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was cooled to room temperature and quenched by water. The resultant product was filtered/extracted with EtOAc to get the product. Crude products were either recrystallized from ethanol or purified by column chromatography using silica as the stationary phase and EtOAc: pet. ether as mobile phase. The products obtained were known compounds and were identified by melting point and 1H and 13C NMR spectroscopy. The spectral data were compared with the literature values.
96% With nitrilo-tris(methylenephosphonic acid) In ethanol; water at 20℃; for 0.166667 h; Green chemistry General procedure: A mixture of 1,2-diamines (1 mmol) and 1,2-dicarbonyls (1 mmol) in ethanol (3 mL)was poured to the solution of NTMPA (5 molpercent, 15 mg) in distilled water (3 mL) atroom temperature. The reaction was monitored by thin-layer chromatography (TLC). Aftercompletion of the reaction, water (10 mL) was added, and the mixture was extracted withdichloromethane (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4, andconcentrated to give the crude product. The crude product was purified by recrystallizationfrom ethanol. All the products were characterized by comparison of their melting pointswith known compounds and 1H NMR spectra.
95%
Stage #1: With ZrOL2(at)SMNP In ethanol at 25℃; for 0.0333333 h;
Stage #2: at 60℃; for 0.05 h;
General procedure: A mixture of the required 1,2-dicarbonyl (1 mmol) and ZrOL2&SMNP (0.004 g) in ethanol (0.5 ml) was stirred at 25°C for 2 min. Then, the required 1,2-diamine (1.5 mmol) was added to the mixture, which was stirred at 60 °C for the appropriate reaction time. The progress of the reaction was monitored by TLC or GC. After completion of the reaction, the precipitate was dissolved by adding ethanol, and ZrOL2&SMNP was separated by decantation of the reaction mixture in the presence of an external magnet. Most of the product was precipitated purely by concentrating and cooling the ethanolic solution. There maining product was isolated from an excess of 1,2-diamine by plate chromatography eluted with n-hexane–EtOAc (10/2). Structural assignments of the products were based on their 1H and 13C NMR spectra.
91% at 20℃; for 0.416667 h; Green chemistry General procedure: A mixture of 1,2-phenylenediamine derivative (1 mmol), 1,2-diketones (1 mmol) and nano SbCl5.SiO2 (62percentw/w ) (0.15 g) was stirred at room temperature under solventless condition. The reaction was monitored by TLC (n-hexane:ethyl acetate, 7:3). After completion of the reaction, the mixture was washed with chloroform (2×5 mL) and filtered to recover the catalyst. The solvent was evaporated and the crude product was recrystallized from ethanol (5 mL) to afford pure quinoxaline derivatives.

Reference: [1] Transition Metal Chemistry, 2010, vol. 35, # 1, p. 49 - 53
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 213 - 218
[3] Catalysis Letters, 2013, vol. 143, # 8, p. 853 - 861
[4] Chinese Journal of Catalysis, 2015, vol. 36, # 8, p. 1379 - 1386
[5] Journal of the Iranian Chemical Society, 2016, vol. 13, # 8, p. 1517 - 1524
[6] Journal of Chemical Sciences, 2017, vol. 129, # 2, p. 141 - 148
[7] Journal of Chemical Sciences, 2013, vol. 125, # 2, p. 353 - 358
[8] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 9, p. 1471 - 1478
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[14] Applied Catalysis A: General, 2011, vol. 394, # 1-2, p. 48 - 51
[15] Monatshefte fur Chemie, 2011, vol. 142, # 6, p. 619 - 624
[16] Heteroatom Chemistry, 2012, vol. 23, # 5, p. 472 - 477
[17] Transition Metal Chemistry, 2013, vol. 38, # 1, p. 31 - 36
[18] Chinese Chemical Letters, 2010, vol. 21, # 4, p. 395 - 398
[19] Russian Chemical Bulletin, 2013, vol. 62, # 5, p. 1244 - 1247[20] Izv. Akad. Nauk, Ser. Khim., 2013, vol. 5, p. 1244 - 1247
[21] Journal of the Chilean Chemical Society, 2015, vol. 60, # 1, p. 2851 - 2856
[22] Chinese Chemical Letters, 2011, vol. 22, # 6, p. 753 - 756
[23] Synthesis (Germany), 2013, vol. 45, # 11, p. 1546 - 1552
[24] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1331 - 1333
[25] Heterocyclic Communications, 2007, vol. 13, # 2-3, p. 125 - 130
[26] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 1, p. 285 - 288
[27] Synthetic Communications, 2012, vol. 42, # 6, p. 883 - 892
[28] Russian Journal of General Chemistry, 1997, vol. 67, # 2, p. 285 - 294
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  • [ 17635-21-1 ]
YieldReaction ConditionsOperation in experiment
81% at 90℃; for 0.25 h; Microwave irradiation General procedure: In a typical reaction, a mixture of arene-1,2-diamine (1 mmol), α-hydroxy ketones (0.5 mmol) and PEG 300 (0.2 g) was mixed thoroughly with 0.10 mmol of [(NH4)6Mo7O24·4H2O] for a few minutes in order to ensure complete homogeneity. The mixture was then inserted into the microwave chamber and the reaction was carried out in an open vessel maintaining the power at 420 W (70percent of maximum power) for 15 min. The reaction mixture was washed with ethyl acetate (10 mL) and the mixture was filtered off. The resulting solid mixture was washed with dichloromethane (10 mL) and filtered. The combined organic medium was subjected to GC in order to find out the conversion and then removed with a rotary evaporator under reduced pressure to afford the product 1. The crude products were purified by column chromatography using ethyl acetate/hexane (2:8 v/v) [dichloromethane/ethanol (9:1 v/v) for products 1f–1j] to afford pure products for analytical measurements. The products were identified by comparison of their NMR and mass spectra with authentic samples.#10;
Reference: [1] Comptes Rendus Chimie, 2012, vol. 15, # 9, p. 764 - 767
[2] Synthetic Communications, 2012, vol. 42, # 2, p. 236 - 245
  • 14
  • [ 496-72-0 ]
  • [ 513-85-9 ]
  • [ 17635-21-1 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 50, p. 6883 - 6886
  • 15
  • [ 7732-18-5 ]
  • [ 64-19-7 ]
  • [ 496-72-0 ]
  • [ 431-03-8 ]
  • [ 17635-21-1 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 1415
  • 16
  • [ 67-56-1 ]
  • [ 496-72-0 ]
  • [ 10394-40-8 ]
  • [ 10394-35-1 ]
  • [ 614-97-1 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 12, p. 5172 - 5181
  • 17
  • [ 50-00-0 ]
  • [ 496-72-0 ]
  • [ 10394-40-8 ]
Reference: [1] Chemische Berichte, 1892, vol. 25, p. 2711
  • 18
  • [ 7647-01-0 ]
  • [ 50-00-0 ]
  • [ 496-72-0 ]
  • [ 10394-40-8 ]
Reference: [1] Chemische Berichte, 1892, vol. 25, p. 2711
[2] Chemische Berichte, 1893, vol. 26, p. 190[3] Chemische Berichte, 1894, vol. 27, p. 2776
  • 19
  • [ 496-72-0 ]
  • [ 39267-05-5 ]
Reference: [1] Helvetica Chimica Acta, 1994, vol. 77, # 6, p. 1549 - 1556
[2] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 20, p. 6433 - 6441
[4] Revue Roumaine de Chimie, 2017, vol. 62, # 12, p. 903 - 906
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1809 - 1814
  • 20
  • [ 496-72-0 ]
  • [ 616-38-6 ]
  • [ 131019-87-9 ]
  • [ 39513-19-4 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1641 - 1643
  • 21
  • [ 496-72-0 ]
  • [ 25625-62-1 ]
Reference: [1] Monatshefte fur Chemie, 2010, vol. 141, # 10, p. 1145 - 1151
  • 22
  • [ 121-14-2 ]
  • [ 618-85-9 ]
  • [ 606-20-2 ]
  • [ 602-01-7 ]
  • [ 610-39-9 ]
  • [ 619-15-8 ]
  • [ 108-71-4 ]
  • [ 823-40-5 ]
  • [ 95-80-7 ]
  • [ 496-72-0 ]
  • [ 95-70-5 ]
  • [ 2687-25-4 ]
Reference: [1] Patent: EP1864969, 2007, A1, . Location in patent: Page/Page column 5; 6
  • 23
  • [ 496-72-0 ]
  • [ 95-75-0 ]
Reference: [1] Journal of the Indian Chemical Society, 1942, vol. 19, p. 497
  • 24
  • [ 496-72-0 ]
  • [ 29289-13-2 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With water; sodium nitrite In neat (no solvent) at 20℃;
Stage #2: With potassium iodide In neat (no solvent) at 20℃;
General procedure: An aromaticamine (1 mmol), nanomagnetic-supported sulfonic acid (c-Fe2O3–SO3H)(0.65 g), NaNO2 (2 mmol, 0.138 g), and 0.2 mL of H2O were homogenized bygrinding in a mortar with a pestle for a few minutes. Formation of a reddishbrowngas was observed as soon as H2O was added. The diazotization reactionlasted for approximately 5–30 min. Next, KI (2.5 mmol, 0.415 g) was added tothe diazonium salt and grinding was continued for 10–20 min. After completionof the reaction, the mixture was triturated with EtOAc (5 mL). The c-Fe2O3–SO3K was separated from the solution using a magnetic bar. The organic layerwas treated with aq 10percent Na2SO3 (15 mL), then dried over anhydrous Na2SO4.After evaporation of the solvent, the crude product was afforded. Purifiedproducts were obtained by recrystallization from ethanol or by flashchromatography (n-hexane–EtOAc, 95:5).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 27, p. 3648 - 3651
  • 25
  • [ 496-72-0 ]
  • [ 65958-37-4 ]
Reference: [1] Russian Journal of General Chemistry, 1997, vol. 67, # 2, p. 285 - 294
  • 26
  • [ 496-72-0 ]
  • [ 102169-44-8 ]
Reference: [1] Journal of Physical Chemistry A, 2016, vol. 120, # 11, p. 1853 - 1866
  • 27
  • [ 60-00-4 ]
  • [ 496-72-0 ]
  • [ 81624-55-7 ]
Reference: [1] Patent: US2008/221146, 2008, A1, . Location in patent: Page/Page column 7-8
  • 28
  • [ 496-72-0 ]
  • [ 130345-50-5 ]
Reference: [1] Patent: WO2006/127458, 2006, A2,
  • 29
  • [ 107-97-1 ]
  • [ 496-72-0 ]
  • [ 887571-32-6 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 3, p. 926 - 932
Same Skeleton Products
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