2-Chloroquinoxaline synthesis
- Product Name:2-Chloroquinoxaline
- CAS Number:1448-87-9
- Molecular formula:C8H5ClN2
- Molecular Weight:164.59
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1448-87-9
The general procedure for the synthesis of 2-chloroquinoxaline from 2-hydroxyquinoxaline is as follows: 2-chloroquinoxaline (1D-008) was efficiently prepared by dissolving 2-hydroxyquinoxaline in pure phosphorus oxychloride (POCl3, 2.3 equiv.) and reacting the reaction under reflux conditions for 1 hour. The reaction has been validated on a 100 g scale, typically yielding 103-105 g of product (98-99% yield). Rapid filtration of the crude reaction mixture through a silica gel pad yields a high purity product (99% purity by LCMS analysis). This reaction has been successfully scaled up to 600 g scale.
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Yield:1448-87-9 93%
Reaction Conditions:
with trichlorophosphate in toluene; for 1 h;Reflux;
Steps:
0 Step 0: Preparation of Precursor Quinaxoline
The chlorination of the 2-hydroxy quinoxaline was carried out in neat POCl3 (2.3 eqs) at reflux for an hour and produced the 2-chloro-quinoxaline (1D-008) in very good yield. This chemistry was tested on 100 g scale and afforded typically 103-105 g (98-99%). A quick filtration through a Pad of silica of the crude reaction mixture resulted in clean material (99% pure by LCMS). This reaction has beenscaled up to 600 g.
References:
US2017/143706,2017,A1 Location in patent:Paragraph 0050; 0106; 0107
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