4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

Base Information

• Chemical Name: 4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• CAS No.: 853105-37-0
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.191
• Hs Code.: 2933399090
• Mol file: 853105-37-0.mol

Synonyms:ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate;4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester;ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate;

Chemical Property of 4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

Chemical Property:

• Vapor Pressure: 3.86E-05mmHg at 25°C
• Melting Point: 117-119°
• Boiling Point: 315.0±42.0 °C(Predicted)
• PKA: 4.50±1.00(Predicted)
• PSA: 68.53000
• Density: 1.335±0.06 g/cm3(Predicted)
• LogP: 0.26760
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

There total 2 articles about 4-HYDROXY-1-METHYL-6-OXO-1,6-DIHYDRO-PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER 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: 85.0%

orthoformic acid triethyl ester (122-51-0) + diethyl 1,3-acetonedicarboxylate (105-50-0) + methylamine (74-89-5) → ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (853105-37-0)

Guidance literature:

orthoformic acid triethyl ester; diethyl 1,3-acetonedicarboxylate; With acetic anhydride; at 135 ℃; for 1h;

methylamine; In water; at 20 ℃;

Reference yield:

diethyl acetylmalonate (570-08-1) + orthoformic acid triethyl ester (122-51-0) → ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (853105-37-0)

Guidance literature:

With acetic anhydride; methylamine; In water;

Reference yield:

ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (853105-37-0) → 4-(4-bromo-2-fluoro-phenylamino)-5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid cyclopropylmethoxy-amide

Guidance literature:

Multi-step reaction with 5 steps

1.1: POCl₃; Et₃N / 16 h

2.1: NCS / dimethylformamide / 1 h / 20 °C

3.1: aq. LiOH / tetrahydrofuran; methanol / 0.5 h / 20 °C

4.1: LDA / tetrahydrofuran; hexane / 0.17 h / -78 °C

4.2: tetrahydrofuran; hexane / 17.5 h / -78 - 20 °C

5.1: EDCI; HOBt / dimethylformamide / 0.5 h / 20 °C

5.2: Et₃N / dimethylformamide / 1 h / 20 °C

With lithium hydroxide; N-chloro-succinimide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm050834y

upstream raw materials:

orthoformic acid triethyl ester

diethyl 1,3-acetonedicarboxylate

methylamine

diethyl acetylmalonate

Downstream raw materials:

ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

ethyl 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

ethyl 4-chloro-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

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