Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate

Base Information

• Chemical Name: Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate
• CAS No.: 389570-71-2
• Molecular Formula: C₁₇H₂₀N₂O₄
• Molecular Weight: 316.357
• Mol file: 389570-71-2.mol

Synonyms:

Chemical Property of Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate

There total 2 articles about Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate 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:

ethylmagnesium bromide (925-90-6) + N-methoxy-N-methylpyridine-3-carboxamide (95091-91-1) + phenyl chloroformate (1885-14-9) → Phenyl 4-ethyl-3-(N-methoxy-N-methylcarbamoyl)-1,4-dihydropyridinecarboxylate + Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate (389570-71-2) + Phenyl 2-ethyl-3-(N-methoxy-N-methylcarbamoyl)-1,4-dihydropyridinecarboxylate

Guidance literature:

N-methoxy-N-methylpyridine-3-carboxamide; phenyl chloroformate; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 0.333333h;

ethylmagnesium bromide; In tetrahydrofuran; for 1h;

DOI:10.1055/s-2001-17509

Reference yield:

nicotinic acid (59-67-6) → Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate (389570-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / HOBt*H₂O; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl; Et₃N / acetonitrile / 2 h / 20 °C

2.1: CuBr*Me₂S / tetrahydrofuran / 0.33 h / -78 °C

2.2: tetrahydrofuran / 1 h

With copper(I) bromide dimethylsulfide complex; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1055/s-2001-17509

Reference yield:

2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) + Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate (389570-71-2) → (1R,2S,7S,8R)-4,5-Dichloro-2,7-dicyano-10-ethyl-12-(methoxy-methyl-carbamoyl)-3,6-dioxo-9-aza-tricyclo[6.2.2.02,7]dodeca-4,11-diene-9-carboxylic acid phenyl ester

Guidance literature:

In Isopropyl acetate; at 20 ℃; for 0.5h;

DOI:10.1055/s-2001-17509

upstream raw materials:

ethylmagnesium bromide

N-methoxy-N-methylpyridine-3-carboxamide

phenyl chloroformate

nicotinic acid