3-Amino-6-chloro-2-picoline Chemical Properties

Melting point:

93-94℃

Boiling point:

232.49°C (rough estimate)

Density 

1.2124 (rough estimate)

refractive index 

1.4877 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

1.79±0.10(Predicted)

form 

Solid

color 

Pale yellow

CAS DataBase Reference

164666-68-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

22-37/38-41-20/21/22

Safety Statements 

26-39-36/37-24/25

RIDADR 

2811

HazardClass 

IRRITANT, TOXIC

HS Code 

29333990

3-Amino-6-chloro-2-picoline Usage And Synthesis

Chemical Properties

Yellow solid

Uses

6-Chloro-2-methylpyridin-3-amine has been used as a reactant in the preparation of Pyrido[3,2-e][1,4]diazepine derivatives with anti-HIV-1-activity.

Synthesis

Step 1: Synthesis of 6-chloro-2-methylpyridin-3-amine (44). 2-Chloro-5-nitro-6-methylpyridine (43, 5 g, 29 mmol) was dissolved in ethanol (20 mL) and concentrated hydrochloric acid was added slowly with stirring. Powdered hydrochloric acid (16.2 g, 289 mmol) and additional concentrated hydrochloric acid (20 mL) were added in batches over 30 minutes at room temperature. After addition, stirring was continued for 30 minutes at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the residue and neutralized with sodium bicarbonate to neutral. Subsequently, ethyl acetate was added for extraction and the two-phase mixture was filtered through diatomaceous earth and washed with ethyl acetate. The organic phase was separated, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated to give the target product 44 (4.1 g, 99% yield) as a yellow solid.

References

[1] Patent: WO2017/4608, 2017, A1. Location in patent: Paragraph 0164
[2] Patent: WO2017/4609, 2017, A1. Location in patent: Paragraph 0235
[3] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[4] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 10, p. 1173 - 1177
[5] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66

3-Amino-6-chloro-2-picoline(164666-68-6)Related Product Information

• 2-(Chloromethyl)pyridine
• 2-Chloro-5-methylpyridine
• 4-Aminopyridine
• 6-Aminocaproic acid
• 6-Chloro-2-picoline
• ALTRENOGEST
• 4-Dimethylaminopyridine
• 2-Amino-6-methylpyridine
• 2-Picoline
• 2-Amino-6-chloropyridine
• 3-Aminopyridine
• 2-Chloro-5-chloromethylpyridine
• 2,6-Lutidine
• 5-Amino-2-methylpyridine
• Glycine
• Tris(hydroxymethyl)aminomethane
• Difluorochloromethane
• 6-Chloro-2-methyl-3-nitropyridine