2-Methoxy-6-(methylamino)pyridine Chemical Properties

Boiling point:

231.5±25.0 °C(Predicted)

Density 

1,09 g/cm³

refractive index 

1.5595

storage temp. 

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

pka

5.04±0.10(Predicted)

form 

clear liquid

color 

Colorless to Light orange to Yellow

InChI

InChI=1S/C7H10N2O/c1-8-6-4-3-5-7(9-6)10-2/h3-5H,1-2H3,(H,8,9)

InChIKey

GXHQLRBOZRJHPZ-UHFFFAOYSA-N

SMILES

C1(NC)=NC(OC)=CC=C1

CAS DataBase Reference

88569-83-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-43-22

Safety Statements 

26-36-36/37

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

2-Methoxy-6-(methylamino)pyridine Usage And Synthesis

Uses

2-Methoxy-6-(methylamino)pyridine is used as an intermediate ingredient in the synthesis of Liranaftate, a topical antifungal agent used primarily for the treatment of skin infections caused by fungi.

Synthesis

General procedure for the synthesis of 2-methoxy-6-(methylamino)pyridine from 2-chloro-6-methoxypyridine and monomethylamine: 2-chloro-6-methoxypyridine (12.0 g, 85.6 mmol) was mixed with 40% aqueous methanamine (24 mL) in a sealed tube and reacted for 7 hr at 170 °C. After completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with 50 mL of water and subsequently extracted with dichloromethane (3 x 50 mL). The organic layers were combined, washed sequentially with 100 mL of water and 100 mL of brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100-200 mesh, eluent 0 to 5% dichloromethane solution in methanol) to afford 6-methoxy-N-methylpyridin-2-amine (2.7 g, 31% yield) as a light yellow oil.1H NMR (400 MHz, CDCl3) δ 7.37 (t, J = 8.0 Hz, 1H), 6.04 (d, J = 8.0 Hz, 1H), 5.94 (d, J = 7.8 Hz, 1H), 4.39 (br. s, 1H), 3.86 (s, 3H), 2.90 (s, 3H).

References

[1] Patent: WO2018/73193, 2018, A1. Location in patent: Page/Page column 49

2-Methoxy-6-(methylamino)pyridine(88569-83-9)Related Product Information

• 2-Methoxy-6-methylaminopyridine
• 5-Amino-2-methoxypyridine
• DIMETHYLAMINOPYRIDINE, POLYMER-BOUND
• 2-Methoxyethanol
• 4-Dimethylaminopyridine
• 2,6-Lutidine
• 2-Methoxypyridine
• Pyridine
• 3-Aminopyridine
• 2-Aminopyridine
• 2-(Trifluoromethoxy)aniline
• 4-Amino-2-methoxypyridine
• (5,6-DIMETHYL-1H-BENZIMIDAZOL-1-YL)ACETIC ACID
• 1-(6-ETHOXYPYRIDIN-2-YL)PIPERAZINE
• Liranaftate
• 1-(6-BUTOXYPYRIDIN-2-YL)PIPERAZINE
• 2-Pyridinemethanamine,4-methoxy-(9CI)
• N-(6-METHOXY-PYRIDIN-2-YL)-2,2-DIMETHYLPROPIONAMIDE