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)...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/154826 |
| _version_ | 1811692821611020288 |
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| author | Pang, Jia Hao Ong, Derek Yiren Chiba, Shunsuke |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Pang, Jia Hao Ong, Derek Yiren Chiba, Shunsuke |
| author_sort | Pang, Jia Hao |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T06:41:53Z |
| format | Journal Article |
| id | ntu-10356/154826 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:41:53Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1548262023-02-28T19:58:53Z C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide Pang, Jia Hao Ong, Derek Yiren Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Acridine Derivative Benzyl Cyanide 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. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by Nanyang Technological University, the Singapore Ministry of Education (Academic Research Fund Tier 2: MOE2019-T2-1-089). 2022-01-12T07:31:52Z 2022-01-12T07:31:52Z 2021 Journal Article 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. https://dx.doi.org/10.15227/ORGSYN.098.0363 0078-6209 https://hdl.handle.net/10356/154826 10.15227/ORGSYN.098.0363 2-s2.0-85118797893 98 363 373 en MOE2019-T2-1-089 Organic Syntheses © 2021 Organic Syntheses, Inc. All rights reserved. This paper was published in Organic Syntheses and is made available with permission of Organic Syntheses, Inc. application/pdf |
| spellingShingle | Science::Chemistry Acridine Derivative Benzyl Cyanide Pang, Jia Hao Ong, Derek Yiren Chiba, Shunsuke C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title | C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title_full | C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title_fullStr | C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title_full_unstemmed | C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title_short | C2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| title_sort | c2 amination of pyridine with primary amines mediated by sodium hydride in the presence of lithium iodide |
| topic | Science::Chemistry Acridine Derivative Benzyl Cyanide |
| url | https://hdl.handle.net/10356/154826 |
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