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98416-72-9 6-Bromo-2-chloro-3-methylquinoxaline 13487186, aquinoxaline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.98416-72-9,6-Bromo-2-chloro-3-methylquinoxaline,as a common compound, the synthetic route is as follows.,98416-72-9

4.11 6-Bromo-3-methyl-2-(phenylthio)quinoxaline (11) To a solution of thiophenol (0.01 mol) in acetonitrile (50 mL), anhydrous potassium carbonate (2.0 g) was added and refluxed for 1 h, then (5, 0.01 mol) was added and the mixture was further refluxed for 12 h (monitored by TLC). After completion of the reaction, the mixture was filtered and the excess of acetonitrile was evaporated under reduced pressure, dried, crystallized from petroleum ether and purified by a silica gel column chromatography (chloroform) to produce crude product. Yield: 78%; (brown powder): mp 59-61 C; IR (KBr) numax in cm-1: 2956, 2851 (aliphatic C-H), 1597 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.65 (s, 3H, CH3), 7.40-7.80 (m, 8H, Ar-H); 13C NMR (DMSO-d6, 125 MHz): delta 20.55 (CH3), 114.23-133.21 (12Ar-C), 154.60, 154.64 (2C=N); MS (m/z), 109 (M+-C9H7N2; 100%), 330 (M+; 3%), 331 (M++1; 6%), 332 (M++2; 3%). Anal. Calcd for C15H11BrN2S (331.23): C, 54.39; H, 3.35; N, 8.46. Found: C, 54.39; H, 3.35; N, 8.46.

98416-72-9 6-Bromo-2-chloro-3-methylquinoxaline 13487186, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Article; Abbas, Hebat-Allah S.; Al-Marhabi, Aisha R.; Eissa, Sally I.; Ammar, Yousry A.; Bioorganic and Medicinal Chemistry; vol. 23; 20; (2015); p. 6560 – 6572;,
Quinoxaline – Wikipedia
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Downstream synthetic route of 98416-72-9

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98416-72-9, 6-Bromo-2-chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,98416-72-9

General procedure: Aminophenol (0.01 mol) was dissolved in a mixture of acetonitrile(50 mL) and DMF (5 mL) containing anhydrous potassium carbonate(2.0 g). The mixture was refluxed for 1 h, then (5, 0.01 mol)was added and the mixture was further refluxed for 6 h (monitoredby TLC). After completion of the reaction, the mixture was filteredand the excess of acetonitrile was evaporated under reduced pressureand crystallized from ethanol to give the correspondingcompounds. 4.12.1 2-[6(7)-Bromo-2-methylquinoxalin-3-yloxy]aniline (12a) The compound 12a was obtained from the reaction of o-aminophenol. Yield: 64%; (orange powder): mp 119-121 C; IR (KBr) numax in cm-1: 3412, 3325 (NH2), 2921, 2825 (aliphatic C-H), 1603 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.75 (s, 3H, CH3), 4.45 (br s, 2H, NH2; exchangeable with D2O), 6.83-7.73 (m, 7H, Ar-H); 13C NMR (DMSO-d6, 125 MHz): delta 20.68 (CH3), 122.60-138.01 (12Ar-C), 143.94, 149.65 (2C=N); MS (m/z), 314 (M+-CH3; 100%), 329 (M+; 35%), 330 (M++1; 13%), 331 (M++2; 34%). Anal. Calcd for C15H12BrN3O (230.18): C, 54.56; H, 3.66; N, 12.73. Found: C, 54.78; H, 3.91; N, 12.63.

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Analyzing the synthesis route of 98416-72-9

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Method B: 4-(4-chlorobenzylideneamino)phenol (0.01 mol) wasdissolved in acetonitrile (50 mL). Anhydrous potassium carbonate(2.0 g) was added to the mixture, which was refluxed for 1 h, then(5, 0.01 mol) was added and the mixture was further refluxed for6 h (monitored by TLC). After completion of the reaction, the mixturewas filtered and the excess of acetonitrile was evaporatedunder reduced pressure to produce the compound, yield; 64%

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General procedure: Method B: 4-[(4-substituted phenylimino)methyl]phenol(0.01 mol) was dissolved in acetonitrile (50 mL). Anhydrous potassiumcarbonate (2.0 g) was added to the mixture, which wasrefluxed for 1 h, then (5, 0.01 mol) was added and the mixturewas further refluxed for 8 h (monitored by TLC). After completionof the reaction, the mixture was filtered and the excess of acetonitrilewas evaporated under reduced pressure to produce the correspondingcompounds

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98416-72-9, 6-Bromo-2-chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,98416-72-9

4.14 4-(-6-Bromo-3-methylquinoxalin-2-yloxy)benzaldehyde (14) p-Hydroxybenzaldehyde (0.01 mol) was dissolved in a mixture of acetonitrile (50 mL) and DMF (5 mL) containing anhydrous potassium carbonate (2.0 g). The mixture was refluxed for 1 h, then compound (5, 0.01 mol) was added and the mixture was further refluxed for 19 h (monitored by TLC). After completion of the reaction, the mixture was filtered and the excess of acetonitrile was evaporated under reduced pressure, dried and crystallized from mixture of benzene and petroleum ether to yield the crude product. Yield: 76%; (orange-brown powder): mp 101-103 C; IR (KBr) numax in cm-1: 2921 (aliphatic C-H), 2837, 2720 (CH-aldehyde), 1697 (C=O), 1597 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.74 (s, 3H, CH3), 7.58-8.04 (m, 7H, Ar-H), 10.04 (s, 1H, CHO); 13C NMR (DMSO-d6, 125 MHz): delta 20.49 (CH3), 122.47-133.54 (12Ar-C), 148.90, 149.52 (2C=N), 190.87 (CHO); MS (m/z), 342 (M+; 100%), 343 (M++1; 27%), 344 (M++2; 96%). Anal. Calcd for C16H11BrN2O2 (343.17): C, 56.00; H, 3.23; N, 8.16. Found: C, 56.19; H, 3.45; N.

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98416-72-9, 6-Bromo-2-chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

98416-72-9, 4.8 6-Bromo-2-hydrazinyl-3-methylquinoxaline (8) To a solution of compound (5, 0.01 mol) in absolute ethanol (50 mL), hydrazine hydrate 90% (0.015 mol) was added and the reaction mixture was refluxed for 10 h (monitored by TLC). After completion of the reaction, the reaction mixture was filtered, dried and crystallized from methanol to give the product. Yield: 86%; (red-brown powder): mp 129-131 C; IR (KBr) numax in cm-1: 3303, 3253, 3144 (NH2, NH), 2920, 2870 (aliphatic C-H), 1596 (C=N); 1H NMR (DMSO-d6, 500 MHz): delta 2.74 (s, 3H, CH3), 4.51 (s, br s, 2H, NH2; exchangeable with D2O), 7.93-8.27 (m, 3H, Ar-H), 9.02 (s, br s, 1H, NH; exchangeable with D2O); 13C NMR (DMSO-d6, 125 MHz): delta 123.33-140.76 (6Ar-C), 147.84, 148.39 (2C=N); MS (m/z), 237 (M+-CH3; 100%), 252 (M+; 40%), 253 (M++1; 10%), 254 (M++2; 38%). Anal. Calcd for C9H9BrN3 (253.10): C, 42.71; H, 3.58; N, 22.14. Found: C, 42.97; H, 3.44; N, 22.32.

The synthetic route of 98416-72-9 has been constantly updated, and we look forward to future research findings.

Downstream synthetic route of 98416-72-9

As the paragraph descriping shows that 98416-72-9 is playing an increasingly important role.

98416-72-9, 6-Bromo-2-chloro-3-methylquinoxaline is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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4.10 7-Bromo-4-methyltetrazolo[1,5-a]quinoxaline (10) Method A: To a solution of (5, 0.01 mol) in absolute ethanol (50 mL), sodium azide (0.01 mol) was added and the reaction mixture was refluxed for two days (monitored by TLC). After completion of the reaction, the mixture was filtered. The solvent was evaporated under reduced pressure to give the product, dried and crystallized from benzene, yield 61%.

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98416-72-9 6-Bromo-2-chloro-3-methylquinoxaline 13487186, aquinoxaline compound, is more and more widely used in various.

INTERMEDIATE: (6-Bromo-3-methyl-quinoxalin-2-yl)-hydrazine (IIo). 4-Bromo-2-fluoro-l- nitro-benzene (40 g), racemic alanine (16.2 g), and K2CO3 (30 g) were refluxed overnight in a mixture of in ethanol (200 mL) and water (200 mL). After cooling to ambient temperature, the mixture was diluted with water, and acidified with 1M aq HCl. The precipitated solid was collected and dried to afford 2-(5-bromo-2-nitro-phenylamino)-propionic acid (41 g). A larger portion of this material prepared in a similar manner (60 g) was dissolved in methanol (250 mL) and treated with SOCI2 (30 mL, added drop-wise). The reaction mixture was stirred at ambient temperature overnight. The volatiles were removed in vacuo. The residue was partitioned between EtOAc and aq NaHC03. The organic layer was dried over MgSO i, filtered, and concentrated in vacuo to afford (5- bromo-2-nitro-phenylamino)-propionic acid methyl ester (60 g). This material was dissolved in AcOH (400 mL), iron powder (55 g) was added, and the mixture was refluxed for 4h. After cooling to ambient temperature, the solid was filtered off and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc and sat. aq NaHC03. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica (eluent: heptanes? EtOAc) to afford 6-bromo-3-methyl-3,4-dihydro-lH-quinoxalin-2-one (47.7 g) as a pale yellow solid. A portion of this material (10 g) was dissolved in THF (150 mL), and the solution was cooled on an ice/water bath. Mn02 (19.3 g) was added. The resulting mixture was stirred at ambient temperature overnight. EtOAc (100 mL) was added to the mixture. The solid was filtered off. The filtrate was concentrated in vacuo to afford 6-bromo-3-methyl-lH-quinoxalin-2-one (8.8 g). A larger portion of this material prepared in a similar manner (10 g) was stirred in PI1POCI2 (80 mL) at 150C for 3h. After cooling to ambient temperature, water was added and pH was adjusted to 7 with aqueous ammonia. The precipitated solid was filtered off, washed with water and dried to afford 6-bromo-2-chloro-3-methyl-quinoxaline (6.67 g). A larger portion of this material prepared in a similar manner (14 g) was dissolved in ethanol (250 mL) and hydrazine hydrate (180 mL) was added. The mixture was refluxed for 3h, cooled to ambient temperature, and most of the volatiles were removed in vacuo. The residue was diluted with water, and solid was filtered off, washed with water, and dried to afford IIo (11.2 g) as a yellow solid sufficiently pure for the next step.

98416-72-9 6-Bromo-2-chloro-3-methylquinoxaline 13487186, aquinoxaline compound, is more and more widely used in various.

Reference£º
Patent; H. LUNDBECK A/S; J?RGENSEN, Morten; BRUUN, Anne, Techau; RASMUSSEN, Lars, Kyhn; LARSEN, Mogens; WO2013/34755; (2013); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider