Methyl 5-hydroxynicotinate

Base Information

• Chemical Name: Methyl 5-hydroxynicotinate
• CAS No.: 30766-22-4
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.137
• Hs Code.: 29333990
• Mol file: 30766-22-4.mol

Synonyms:Nicotinicacid, 5-hydroxy-, methyl ester (7CI,8CI);3-Hydroxy-5-methoxycarbonylpyridine;5-Hydroxy-3-pyridinecarboxylic acid methyl ester;5-Hydroxynicotinic acidmethyl ester;NSC 605540;3-Pyridinecarboxylicacid, 5-hydroxy-, methyl ester;

Chemical Property of Methyl 5-hydroxynicotinate

Chemical Property:

• Appearance/Colour: Light beige powder and lumps
• Vapor Pressure: 3.95E-06mmHg at 25°C
• Melting Point: 190 °C
• Refractive Index: 1.551
• Boiling Point: 374.192 °C at 760 mmHg
• PKA: 8.44±0.10(Predicted)
• Flash Point: 180.105 °C
• PSA: 59.42000
• Density: 1.287 g/cm³
• LogP: 0.57380
• Storage Temp.: Keep Cold
• Solubility.: DMSO (Heated, Sonicated), Methanol (Slightly, Sonicated)

Purity/Quality:

Methyl 5-Hydroxynicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5-Hydroxynicotinate is an intermediate used to prepare selective cyclooxygenase-2 inhibitors. It is also used to prepare imino sugars as inhibitors of liver glycogen phosphorylase.

Technology Process of Methyl 5-hydroxynicotinate

There total 4 articles about Methyl 5-hydroxynicotinate 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%

methanol (67-56-1) + 5-hydroxynicotinic acid (27828-71-3) → methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4)

Guidance literature:

With sulfuric acid; In methanol; at 30 ℃; for 168h; Inert atmosphere; Reflux;

Reference yield: 77.0%

methyl 5-benzyloxy-4-chloronicotinate (958266-11-0) → methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; at 20 ℃; for 0.666667h;

DOI:10.1002/ejoc.200700333

Reference yield:

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) → methyl 5-hydroxy-3-pyridinecarboxylate (30766-22-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 50 ℃; for 3h;

DOI:10.1016/j.bmcl.2011.03.022

upstream raw materials:

methanol

5-hydroxynicotinic acid

methyl 5-benzyloxy-4-chloronicotinate

5-bromo-3-pyridine carboxylic acid methyl ester

Downstream raw materials:

methyl 5-(4-methoxycarbonyl-2-nitrophenoxy)nicotinate

5-hydroxy-nicotinic acid tert-butyl ester

methyl 5-hydroxypiperidine-3-carboxylate

1-(1,1-dimethylethyl) 3-methyl 5-hydroxy-1,3-piperidinedicarboxylate

Refernces

• 1、 -. "MEVALONATE PATHWAY INHIBITOR AS HIGHLY-EFFECTIVE VACCINE ADJUVANT". Paragraph 0347; 0348. . Retrieved 2018/08/01.
• 2、 -. "BICYCLIC HYDROXAMIC ACIDS USEFUL AS INHIBITORS OF MAMMALIAN HISTONE DEACETYLASE ACTIVITY". Page/Page column 113. . Retrieved 2017/07/14.