ChemicalBook CAS DataBase List 4-METHYL-2-M-TOLYL-PYRIDINE

4-METHYL-2-M-TOLYL-PYRIDINE synthesis

4synthesis methods

Product Name:4-METHYL-2-M-TOLYL-PYRIDINE
CAS Number:80635-91-2
Molecular formula:C13H13N
Molecular Weight:183.25

591-17-3 Synthesis

591-17-3
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301652-23-3
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80635-91-2
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Yield:80635-91-2 66%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in toluene; for 72 h;Inert atmosphere;Reflux;

Steps:

1.a

2-tributylstannylpyridine (6.02 g, 16.3 mmol), 1-bromo-2-methylbenzene (6.63 g, 38.8 mmol) and Pd(PPh₃)₄ (0.613 g, 0.003 equivalent) were refluxed in toluene (150 mL) and under an argon atmosphere for 72 hours. Next, the obtained solution was cooled to room temperature, the reaction system was concentrated, 6M-HCl (50 ml) was added, and extraction with methylene chloride (100 mL) was carried out three times to remove components such as raw materials and pyridyl derivatives as byproducts. Successively, an aqueous ammonium solution (28%) was added to the obtained water phase to neutralize the water phase. Continuously, an excess amount of NiCl₂-6H₂O was added to the obtained solution and extraction with methylene chloride (100 mL) was carried out three times to obtain a brown solution. Next, the obtained brown solution was dried with Na₂SO₄ and filtered with filter paper and the filtrate was concentrated under reduced pressure to obtain a brown oily product. Furthermore, the brown oily product was refined with a silica gel column (ethyl acetate) to obtain a finally aimed compound; 2-(2'-methylphenyl)-4-methylpyridine (2.0 g, 10.7 mmol) (yield: 66%).

References:

EP2275494,2011,A1 Location in patent:Page/Page column 24

4926-28-7 Synthesis