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Title: C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide
Authors: Pang, Jia Hao
Ong, Derek Yiren
Chiba, Shunsuke
Keywords: Science::Chemistry
Issue Date: 2021
Source: Pang, J. H., Ong, D. Y. & Chiba, S. (2021). C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide. Organic Syntheses, 98, 363-373.
Project: MOE2019-T2-1-089
Journal: Organic Syntheses
Abstract: 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.
ISSN: 0078-6209
DOI: 10.15227/ORGSYN.098.0363
Schools: School of Physical and Mathematical Sciences 
Rights: © 2021 Organic Syntheses, Inc. All rights reserved. This paper was published in Organic Syntheses and is made available with permission of Organic Syntheses, Inc.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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