3-Amino-2-chloro-4-methylpyridine Chemical Properties

Melting point:

65-70 °C

Boiling point:

283.3±35.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform, Ethanol

pka

3.22±0.10(Predicted)

form 

Crystals

color 

Off White

InChI

InChI=1S/C6H7ClN2/c1-4-2-3-9-6(7)5(4)8/h2-3H,8H2,1H3

InChIKey

UOBCYTOUXLAABU-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(C)=C1N

CAS DataBase Reference

133627-45-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36/37/39-36-39

RIDADR 

UN2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

3-Amino-2-chloro-4-methylpyridine Usage And Synthesis

Chemical Properties

Off White Crystals

Uses

3-Amino-2-chloro-4-methylpyridine, also known as CAPIC, is a key intermediate in the production of nevirapine, a non-nucleosidic reverse transcriptase inhibitor that has been established to be clinically useful for the treatment of infection by HIV-1.

Preparation

An improved and commercially valuable process is developed by Ge et al. for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. Specifically, a stirred solution of NaOH (15.6 g, 0.39 mol) and water (85 g) at 10 ℃ was added, 10% NaClO (96.8 g, 0.13 mol) and ethanol (80 g). 2-Chloro-3-amido-4- methylpyridine 7 (22 g, 0.13 mol) was added to the reaction mixture, stirring for 1 h. The mixture was heated to 60 ℃ and held for 3 h. After ethanol was removed in a vacuum, the mixture was cooled with an ice-water bath for 15–20 min to precipitate solid. Then, the mixture was filtered, washed with water, and dried to give 15.8 g (85.1% yield) of light yellow solid. 14.7 g of the white solid 2 was obtained via recrystallization in toluene.

References

[1] Xin Ge. “A concise synthesis of 2-chloro-3-amino-4-methylpyridine.” Research on Chemical Intermediates 37 6 (2011): 599–604.

3-Amino-2-chloro-4-methylpyridine(133627-45-9)Related Product Information

• 6-Aminocaproic acid
• Pyridine
• DIMETHYLAMINOPYRIDINE, POLYMER-BOUND
• 4-Dimethylaminopyridine
• 2-Aminopyridine
• 2-Chloro-3-pyridinamine
• 3-Amino-4-methylpyridine
• 2-Chloro-5-chloromethylpyridine
• METSULFURON METHYL
• 4-Methylpyridin-2-amine
• 4-Aminopyridine
• 3-Aminopyridine
• Glycine
• Tribenuron methyl
• Thiophanate-methyl
• Methyl acetate
• 2-Chloro-3-picoline
• 2-Chloro-4-methyl-3-nitropyridine