ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate
• CAS No.: 77276-17-6
• Molecular Formula: C12H12N2O4
• Molecular Weight: 248.23
• Hs Code.: 2933990090
• Mol file: 77276-17-6.mol

Synonyms:4-hydroxy-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester;ethyl4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate;A9781;

Chemical Property of ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Chemical Property:

• PSA: 81.42000
• LogP: 0.81580
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

There total 5 articles about ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate 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: 67.0%

ethyl 2-(methylamino)pyridine-3-carboxylate (103976-61-0) + ethyl chlorocarbonylacetate (36239-09-5) → ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3- carboxylate (77276-17-6)

Guidance literature:

ethyl 2-(methylamino)pyridine-3-carboxylate; ethyl chlorocarbonylacetate; With dmap; In tetrahydrofuran; at 0 - 20 ℃; for 0.333333h;

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃;

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bmc.2020.115376

Reference yield:

N-methyl 2H-pyrido<2,3-d><1,3>oxazine-2,4-1H-dione (53890-44-1) + diethyl malonate (105-53-3) → ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3- carboxylate (77276-17-6)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1) dimethylacetamide, 2) 120 deg C, 18 h;

Reference yield:

ethyl 2-chloronicotinate (1452-94-4) → ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3- carboxylate (77276-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 3 h / 40 °C

2.1: dmap / tetrahydrofuran / 0.33 h / 0 - 20 °C

2.2: 20 °C

2.3: 3 h / 0 - 20 °C

With dmap; In tetrahydrofuran;

DOI:10.1016/j.bmc.2020.115376

upstream raw materials:

N-methyl 2H-pyrido<2,3-d><1,3>oxazine-2,4-1H-dione

diethyl malonate

methyl 2-(methylamino)nicotinate

ethyl chlorocarbonylacetate

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