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Short Note

4-Hydroxy-6-methyl-3-nitroso-1-phenethyl-2(1H)-pyridinone

by
Edmont V. Stoyanov
* and
Ivo C. Ivanov
Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgaria
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(1), M132; https://doi.org/10.3390/M132
Submission received: 10 January 2000 / Accepted: 14 January 2000 / Published: 24 January 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 05 m132 i001
The starting 4-hydroxy-6-methyl-1-phenethyl-2(1H)-pyridinone (1) was prepared according to the known procedure [1,2]. To a suspension of the pyridinone 1 (2.29 g, 10 mmol) in concentrated hydrochloric acid (15 ml), was added dropwise a solution of sodium nitrite (620 mg, 9 mmol) in water (8 ml) with stirring at 20–25 °C. The reaction mixture was stirred for further 10 min. The crystals that separated were filtered off, washed twice with cold water and dried (2 h at 70–80 °C) to afford the title compound 2. Yield after recrystallization from methanol: 1.71 g (71 %). Brown needles, m.p. 148 °C (dec.) (methanol).
1H NMR (100 MHz, CDCl3): 2.10 (s, 3H, 6-CH3), 2.99 (t, J = 7.0 Hz, 2H, 1-CH2CH2Ph), 4.11 (t, J = 7.7 Hz, 2H, 1-CH2CH2Ph), 5.63 (s, 1H, H-5), 7.26 (m, 5H arom., C6H5).
FT IR (nujol): 1700, 1634, 1578, 1540, 1364, 1308, 1256, 1183, 1152, 1111, 1082, 974, 833, 750, 702.
EI MS (70 eV; m/z (%)): 258 (M+., 12), 244 (15), 242 (8), 227 (3), 214 (8), 201 (1), 197 (2), 186 (7), 154 (18), 140 (92), 123 (16), 110 (36), 105 (56), 104 (100), 96 (63), 91 (30), 77 (34), 65 (19), 55 (34), 44 (90).
Anal. calcd. for C14H14N2O3 (258.27): C 65.10, H 5.50, N 10.80; Found C 64.84, H 5.46, N 10.83.

Supplementary Materials

References

  1. Ivanov, I.C.; Stoyanov, E.V.; Alexandrova, S.V.; Oka, S.; Ohno, A. Farmatsiya (Sofia) 1997, 44 (2), 3-6. C.A. 1988, 128, 243925w.
  2. Castillo, S.; Ouadahi, H.; Herault, V. Bull. Soc. Chim. Fr. 1982, II-257-261.
Sample Availability: Available from the authors.

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MDPI and ACS Style

Stoyanov, E.V.; Ivanov, I.C. 4-Hydroxy-6-methyl-3-nitroso-1-phenethyl-2(1H)-pyridinone. Molecules 2000, 5, M132. https://doi.org/10.3390/M132

AMA Style

Stoyanov EV, Ivanov IC. 4-Hydroxy-6-methyl-3-nitroso-1-phenethyl-2(1H)-pyridinone. Molecules. 2000; 5(1):M132. https://doi.org/10.3390/M132

Chicago/Turabian Style

Stoyanov, Edmont V., and Ivo C. Ivanov. 2000. "4-Hydroxy-6-methyl-3-nitroso-1-phenethyl-2(1H)-pyridinone" Molecules 5, no. 1: M132. https://doi.org/10.3390/M132

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