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2-(Methylamino)pyridine-3-methanol

CAS No.32399-12-5
Chemical Name:2-(Methylamino)pyridine-3-methanol
CBNumber:CB4966256
Molecular Formula:C7H10N2O
Formula Weight:138.17
MOL File:32399-12-5.mol

2-(Methylamino)pyridine-3-methanol Property

Boiling point 312.2±32.0 °C(Predicted)
Density 1.191±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka 13.63±0.10(Predicted)
InChI InChI=1S/C7H10N2O/c1-8-7-6(5-10)3-2-4-9-7/h2-4,10H,5H2,1H3,(H,8,9)
InChIKey VYPMWCUNCNMNOM-UHFFFAOYSA-N
SMILES C1(NC)=NC=CC=C1CO

Safety

Safety Statements :24/25
HS Code :29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H332-H335
Precautionary statements P280-P305+P351+P338-P310

2-(Methylamino)pyridine-3-methanol Chemical Properties,Usage,Production

Description 2-(Methylamino)pyridine-3-methanol is an industrial chemical that is used as a solvent and in the production of potassium sulfate. It has a high boiling point, which makes it a good choice for large-scale industrial processes. 2-(Methylamino)pyridine-3-methanol is also an organic solvent, which can be used to dissolve many other molecules.
Uses 2-(Methylamino)pyridine-3-methanol is a raw material for the synthesis of isavuconazolium sulfate (triazole antifungal drug).
Preparation Method 1: 2-Chloronicotinic acid is used as the starting material, reacted with methylamine hydrochloride, potassium carbonate, and cuprous bromide in DMF solvent at 100°C to prepare 2-methylamino-3-pyridinecarboxylic acid, and then reduced with lithium aluminium hydride to obtain the target product 2-(Methylamino)pyridine-3-methanol.
Method 2: 2-Methylamino-3-pyridinecarboxylic acid tert-butyl ester is reduced to the 2-methylamino-3-pyridinemethanol in an organic solvent and the presence of sodium borohydride/Lewis acid or potassium borohydride/Lewis acid reducing agent. 180 mL of tetrahydrofuran, 11.4 g (0.300 mol) of potassium borohydride, and 20.5 g (0.150 mol) of zinc chloride are added to a 500 mL three-necked flask and stirred at room temperature for 2 hours. Add 25g (0.120mol) of tert-butyl 2-methylamino-3-pyridinecarboxylate and 84mL of toluene. During the addition process, bubbles are released, and the addition rate is controlled. Keep reflux until the addition and reaction are complete. Then cool to room temperature and add 20% sodium hydroxide solution until the solution is clear. Then add ethyl acetate 500mL*3 to extract three times, combine the organic phases, wash twice with saturated brine 250mL*2, dry with anhydrous sodium sulfate, and spin dry to obtain 2-methylamino-3-pyridinemethanol as a white solid. Then, recrystallize from isopropanol/n-hexane to obtain 13.0g of a white solid with a yield of 88.2%.

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