C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide

C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide

N-Butylpyridin-2-amine (3). An oven-dried, 250 mL three-necked roundbottomed flask fitted with a 25 x 15 mm Teflon-coated oval magnetic stir bar, a thermometer, rubber septum and a Liebig reflux condenser, is connected to a Schlenk line (Note 2). Sodium hydride (NaH) (3.00 g, 75.0 mmol, 3.0 equiv)...

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Bibliographic Details
Main Authors: Pang, Jia Hao, Ong, Derek Yiren, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Acridine Derivative
Benzyl Cyanide
Online Access:https://hdl.handle.net/10356/154826
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Institution: Nanyang Technological University
Language: English
Description
Summary:N-Butylpyridin-2-amine (3). An oven-dried, 250 mL three-necked roundbottomed flask fitted with a 25 x 15 mm Teflon-coated oval magnetic stir bar, a thermometer, rubber septum and a Liebig reflux condenser, is connected to a Schlenk line (Note 2). Sodium hydride (NaH) (3.00 g, 75.0 mmol, 3.0 equiv) (Note 3) is charged to the reaction vessel, after which it is evacuated and backfilled with argon three times. Anhydrous THF (Note 4) (35 mL) is added via a syringe. The reaction flask is suspended in a 22 °C water bath, and lithium iodide (LiI) (6.69 g, 50.0 mmol, 2.0 equiv) (Note 5) is introduced through the top of the reflux condenser, after which the Ar line is reintroduced with an out needle in place for 5 min to exchange the atmosphere.

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