Pyridine, 3-methoxy-2-phenyl-

Base Information

• Chemical Name: Pyridine, 3-methoxy-2-phenyl-
• CAS No.: 53698-49-0
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Mol file: 53698-49-0.mol

Synonyms:

Chemical Property of Pyridine, 3-methoxy-2-phenyl-

Chemical Property:

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Technology Process of Pyridine, 3-methoxy-2-phenyl-

There total 10 articles about Pyridine, 3-methoxy-2-phenyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-bromo-3-methoxypyridine (24100-18-3) + phenylboronic acid (98-80-6) → 3-methoxy-2-phenylpyridine (53698-49-0)

Guidance literature:

With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; butan-1-ol; at 100 ℃; for 8h;

DOI:10.1002/adsc.200900848

Reference yield: 94.0%

N-(3-methoxy-2-phenyl-2H-pyridin-1-yl)-N-methyl-benzamidine → 3-methoxy-2-phenylpyridine (53698-49-0)

Guidance literature:

N-(3-methoxy-2-phenyl-2H-pyridin-1-yl)-N-methyl-benzamidine; With manganese triacetate; acetic acid; at 60 ℃; for 2h;

With water; acetic acid; at 80 ℃;

DOI:10.1021/ol048624n

Reference yield: 94.0%

2-chloro-3-methoxypyridine (52605-96-6) + phenylboronic acid (98-80-6) → 3-methoxy-2-phenylpyridine (53698-49-0)

Guidance literature:

2-chloro-3-methoxypyridine; phenylboronic acid; With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl; In dodecane; butan-1-ol; at 25 ℃; for 0.25h; Inert atmosphere; Glovebox;

With cesiumhydroxide monohydrate; In dodecane; water; butan-1-ol; at 25 ℃; Inert atmosphere; Glovebox;

DOI:10.1002/ejoc.201200918

upstream raw materials:

3-methoxypyridine

N-methylbenzamide

2-bromo-3-methoxypyridine

phenylboronic acid

Downstream raw materials:

2-[3-(hexan-2-yl)-phenyl]-3-methoxypyridine

diisopropyl (2-(3-methoxypyridin-2-yl)phenyl)phosphonate

3-methoxy-2-(3-nitrophenyl)pyridine

Refernces

REACTIONS OF N-(4-METHOXYBENZYLIDENE)-N,N-DIALKYLIMINIUM AND 2-(4-METHOXYPHENYL)PYRIDINIUM SALTS WITH ALIPHATIC AMINES

10.1007/BF00472485

The research investigates the reactions of N-(4-methoxybenzylidene)-N,N-dialkyliminium and 2-(4-methoxyphenyl)pyridinium salts with aliphatic amines. Key chemicals involved include 2-(4-methoxyphenyl)pyridinium salts (IIa, b) and N-(4-methoxybenzylidene)-N,N-dialkyliminium salts (IIIa, b), which were synthesized from appropriate Schiff bases of methoxyphenylpyridine. The study explores how these compounds react with various aliphatic amines such as methylamine, dimethylamine, and piperidine under different conditions. For instance, heating pyridinium salt (IIa) with methylamine in ethanol at 140°C for 40 hours results in SN2-dealkylation of the pyridine ring. The iminium salts (IIIa, b) react with methylamine at ambient temperature to undergo transamination, yielding Schiff bases and unstable aminals. When heated with alcoholic amines, these salts undergo aromatic nucleophilic substitution, producing corresponding aldehydes upon hydrolysis. The research also examines the reaction of these salts with piperidine, which leads to the formation of bis(methoxybenzyl)pyridine (VIII) under specific conditions. The study provides insights into the reactivity of these compounds and their potential applications in organic synthesis.

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