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Volume 2006
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Short Note

Synthesis of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol

by
Craig A. Obafemi
1,*,
Wolfgang Pfleiderer
2 and
Festus Taiwo
1
1
1Department of Chemistry, Obafemi Awolowo University, Ile-Ife, Nigeria
2
Fachbereich Chemie, Konstanz University D-78457 Konstanz/Germany
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(6), M508; https://doi.org/10.3390/M508
Submission received: 7 February 2005 / Accepted: 2 February 2006 / Published: 1 December 2006
Versions Notes

Molbank 2006 m508 i001
A mixture of 2,3-dichloroquinoxaline 1[1] (5.0 g, 25 mmol) and diethanolamine 2 (12 mL, 125 mmol) was heated to 130° C for 3 h, with magnetic stirring. The reaction mixture was cooled to room temperature and then poured into 300 mL of water. The resulting solid was filtered and then recrystallized from water to give white crystals of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol 3 (5.3 g, 91%).
Melting point: 159 – 161°C. (Ref. [2]: 88%, m.p. 158°C)
IR (nmax, KBr, cm-1): 3295 (OH), 1530, 1350, 1205, 1060
1H-NMR (400 MHz, CDCl3, d (ppm): 7.58 – 7.52 (m, 2H, Ar-H), 7.41 (t, 1H, Ar-H), 7.29 (t, 1H, Ar-H), 4.86 (t, 1H, OH, D2O exchangeable), 4.48 (t, 2H, CH2), 3.80 – 3.72 (m, 6H, (3 x CH2) ).
13C-NMR (100 MHz, CDCl3, d (ppm): 147.5, 142.7, 139.2, 134.9, 126.7, 126.1, 124.7, 123.8, 64.3, 58.1, 49.9, 46.2
MS (m/z, %): 231 (M+, 35.7), 212 ([M-H3O.]+, 6.0), 201 ([M - HCHO]+, 26.4), 200 ([M - CH2OH]+, 100), 187 ([M - CH2 = CHOH]+, 70.9), 129 (24.8), 90 (15.2), 56 (41.5).

Supplementary Materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

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

References

  1. Obafemi, C.A.; Pfleiderer, Wolfgang. Helv. Chim. Acta 1994, 77, 1549–1556. [CrossRef]
  2. Goncharova, I.N.; Postovskii, I. Ya. J. J. Gen. Chem. USSR 1962, 32, 3271–3278, 1H-NMR, 13C-NMR and mass spectra data are not given in this paper.

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MDPI and ACS Style

Obafemi, C.A.; Pfleiderer, W.; Taiwo, F. Synthesis of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol. Molbank 2006, 2006, M508. https://doi.org/10.3390/M508

AMA Style

Obafemi CA, Pfleiderer W, Taiwo F. Synthesis of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol. Molbank. 2006; 2006(6):M508. https://doi.org/10.3390/M508

Chicago/Turabian Style

Obafemi, Craig A., Wolfgang Pfleiderer, and Festus Taiwo. 2006. "Synthesis of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol" Molbank 2006, no. 6: M508. https://doi.org/10.3390/M508

APA Style

Obafemi, C. A., Pfleiderer, W., & Taiwo, F. (2006). Synthesis of 2-(1,4-oxazino[2,3-b]quinoxalin-4-yl)ethanol. Molbank, 2006(6), M508. https://doi.org/10.3390/M508

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