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Volume 2006
Issue 6
10.3390/M509
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Short Note

Synthesis of N, N-Dimethyl-3-phenoxyquinoxalin-2-amine

by
Craig A. Obafemi
1,* and
Wolfgang Pfleiderer
2
1
1Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
2
2Fachbereich Chemie, Konstanz University D-78457 Konstanz/ Germany
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(6), M509; https://doi.org/10.3390/M509
Submission received: 7 February 2005 / Accepted: 2 February 2006 / Published: 1 December 2006
Versions Notes

The two chloro groups in 2,3-dichloroquinoxaline 1 can be displaced by nucleophiles, a process that may take place in a stepwise manner [1]. 1 was reacted with phenol 2 in dimethylformamide (DMF) to give N,N-dimethyl-3-phenoxyquinoxalin-2-amine 3.
Molbank 2006 m509 i001
A mixture of 2,3-dichloroquinoxaline 1 (5.0 g, 25 mmol), phenol (1.2 g, 13 mmol) and Na2CO3 (0.7 g, 7 mmol) in DMF (40 mL) was heated to reflux for 10 h. with magnetic stirring. The reaction mixture was cooled and poured into water (200 mL) to give a solid product. Flash vacuum column chromatography (silica gel, petroleum ether (b.p. 100°)/EtOH 100:1) gave pure N,N-dimethyl-3-phenoxyquinoxalin-2-amine 3 (2.1 g, 62%, based on phenol).
Melting point: 85 – 86°C.
IR (nmax, KBr, cm-1): 2940, 2880 (C-H), 1578 (C=C), 1516, 1196.
1H-NMR (400 MHz, CDCl3, d (ppm): 7.72 (d, 1H, J = 8.47 Hz, Ar-H), 7.52 (d, 1H, J = 9.25 Hz, Ar-H), 7.47 – 7.34 (m, 3H, Ar-H), 7.31 – 7.21 (m, 4H, Ar-H), 3.31 (s, 6H, 2 x CH3).
13C-NMR (100 MHz, CDCl, d (ppm): 152.9, 149.6, 147.7, 139.5, 135.4, 129.5, 127.3, 126.6, 125.7, 125.0, 124.9, 121.6, 40.6.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

We thank the Alexander von Humboldt Foundation for a post-doctoral fellowship (CAO).

Reference

  1. Obafemi, C.A.; Pfleiderer, W. Molecules 2004, 9, 229–237.

Share and Cite

MDPI and ACS Style

Obafemi, C.A.; Pfleiderer, W. Synthesis of N, N-Dimethyl-3-phenoxyquinoxalin-2-amine. Molbank 2006, 2006, M509. https://doi.org/10.3390/M509

AMA Style

Obafemi CA, Pfleiderer W. Synthesis of N, N-Dimethyl-3-phenoxyquinoxalin-2-amine. Molbank. 2006; 2006(6):M509. https://doi.org/10.3390/M509

Chicago/Turabian Style

Obafemi, Craig A., and Wolfgang Pfleiderer. 2006. "Synthesis of N, N-Dimethyl-3-phenoxyquinoxalin-2-amine" Molbank 2006, no. 6: M509. https://doi.org/10.3390/M509

APA Style

Obafemi, C. A., & Pfleiderer, W. (2006). Synthesis of N, N-Dimethyl-3-phenoxyquinoxalin-2-amine. Molbank, 2006(6), M509. https://doi.org/10.3390/M509

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