152362-01-1

Basic information

• Product Name: 2-chloro-4-methylpyridine-3-carboxamide
• Synonyms: 2-chloro-4-methylpyridine-3-carboxamide;3-PyridinecarboxaMide, 2-chloro-4-Methyl-;2,4-diMethylpyridine-3-carboxaMide;2-Chloro-4-methyl-3-pyridinecarboxamide
• CAS NO: 152362-01-1
• Molecular Formula: C₇H₇ClN₂O
• Molecular Weight: 170.59628
• EINECS: -0
• Mol File: 152362-01-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 176.4-177.9 °C
• Boiling Point: 289℃
• Flash Point: 129℃
• Appearance: /
• Density: 1.316
• Storage Temp.: 2-8°C
• PKA: 14.21±0.50(Predicted)
• CAS DataBase Reference: 2-chloro-4-methylpyridine-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-4-methylpyridine-3-carboxamide(152362-01-1)
• EPA Substance Registry System: 2-chloro-4-methylpyridine-3-carboxamide(152362-01-1)

Safety Data

• Hazardous Substances Data: 152362-01-1(Hazardous Substances Data)

Usage

Uses

2-Chloro-4-methylnicotinamide can be used to prepare Nevirapine, a HIV drug substance.

Upstream product

• 65169-38-2 2-chloro-4-methyl-3-pyridinecarbonitrile 
• 13166-10-4 isopropylidenemalonodinitrile 
• 71493-72-6 2-(4-(dimethylamino)but-3-en-2-ylidene)malononitrile 
• 93271-59-1 2-hydroxy-4-methylpyridine-3-carbonitrile 
• 152362-00-0 ethyl 2-chloro-2-cyano-3-methyl-5-oxopentanoate 
• 142266-63-5 2-chloro-4-methyl-3-pyridinecarboxylic acid 
• 50840-02-3 ethyl 2-chloro-4-methyl-3-pyridinecarboxylate 
• 50839-95-7 2-chloro-4-methylnicotinoylchloride 

Downstream Products

• 129618-40-2 Nevirapine 
• 133627-47-1 N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide 
• 133627-45-9 3-Amino-2-chloro-4-methylpyridine 

Relevant articles and documents

Increasing global access to the high-volume HIV drug nevirapine through process intensification

Access to affordable medications continues to be one of the most pressing issues for the treatment of disease in developing countries. For many drugs, synthesis of the active pharmaceutical ingredient (API) represents the most financially important and technically demanding element of pharmaceutical operations. Furthermore, the environmental impact of API processing has been well documented and is an area of continuing interest in green chemical operations. To improve drug access and affordability, we have developed a series of core principles that can be applied to a specific API, yielding dramatic improvements in chemical efficiency. We applied these principles to nevirapine, the first non-nucleoside reverse transcriptase inhibitor used in the treatment of HIV. The resulting ultra-efficient (91% isolated yield) and highly-consolidated (4 unit operations) route has been successfully developed and implemented through partnerships with philanthropic entities, increasing access to this essential medication. We anticipate an even broader global health impact when applying this model to other active ingredients.

A pyridine amide synthetic method of compound

The invention discloses a method for synthesizing a pyridine-amide compound. The method comprises the steps of carrying out hydrolysis on a pyridine cyanogen compound shown by a formula II as a starting material in water as a solvent in the presence of an ETS-10 molecular sieve as a catalyst, heating to 100-150 DEG C, reacting until the reaction, which is tracked and detected by virtue of TLC (Thin-Layer Chromatography), is completed and carrying out post-treatment on the reaction solution to obtain the pyridine-amide compound represented by the formula I. According to the method disclosed by the invention, the ETS-10 molecular sieve is taken as a catalyst to carry out hydrolysis on pyridine cyanogen to obtain a single pyridine-amide product, the conversion rate is 100%, the yield is above 95% and the catalyst can be repeatedly used for at least 5 times.

Improved synthesis of 2-chloro-3-amino-4-methylpyridine

2-Chloro-3-amino-4-methylpyridine (), a key intermediate in the synthesis of nervirapine, was prepared from 2-cyanoacetamide and 4,4-dimethoxyl-2-butanone via condensation, cyclization, one-pot reaction of chlorination and hydrolysis, and Hofmann reaction. Utilization of the quadratic orthogonal test resulted in a high yield (62.1%) of the whole process.