Next Article in Journal
Ethyl-(R,S)-5-acetyl-4,5-dihydro-3-isoxazole Acetate
Previous Article in Journal
a,a,a',a'- Tetra(5-methylfur-2-yl)-p-xylene
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

1-Methyl-3-nitro-5-methoxycarbonyl Pyrazole

Department of Pharmaceutical Sciences, University of Ferrara, Via Fossato di Mortara 17-19, I-44100 Ferrara, Italy
*
Author to whom correspondence should be addressed.
Molecules 1998, 3(2), M46; https://doi.org/10.3390/M46
Submission received: 3 February 1998 / Published: 18 February 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 03 m46 i001
The nitroester 2 was prepared by the addition of meta-chloro-perbenzoic acid (m-CPBA) to 1 [1] according to the reported procedure [2,3].
To a stirred solution of 1 (524 mg, 3.67 mmol) in dry CHCl3 (9 mL), heated at 70 °C, m-CPBA (3.18 g, 14.8 mmol, 4 eq) dissolved in dry CHCl3 (23 ml), was added. After 1 h, TLC analysis (AcOEt, Rf 0.5), showed the disappearance of the starting material. The mixture was cooled and filtered through a pad of celite. The filtrate, was washed twice with aqueous 10% NaOH and the organic phase was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by crystallization (light petroleum/ether) to afford 2 as a white solid (476 mg, 75%).
M.p. 66-68 °C.
TLC (AcOEt/light petroleum 7:3) Rf 0.37.
IR (KBr, cm−1): 1730, 1550, 1380, 1330, 1300, 1270, 1130, 1090, 1000, 840, 760, 750.
1HNMR (CDCl3) d: 7.40 (s, 1H, CH); 4.29 (s, 3H, CO2CH3); 3.96 (s, 3H, N-CH3).
Anal. calc. for C6H7N3O4 (185.14): C 38.93, H 3.81, N 22.70; found: C 38.71, H 3.89, N 22.89.

Supplementary Materials

The following supporting information can be downloaded at: www.mdpi.com/xxx/s1.

Acknowledgments

We gratefully acknowledge the Ministero Pubblica Istruzione (Grant 40% and 60%) for their generous support.

References

  1. Lee, H.H.; Boyd, M.; Gravatt, G.L.; Denny, W.A. Pyrazole analogues of the bispyrrolecarboxamide anti-tumour antibiotics: synthesis, DNA binding and anti-tumour properties. Anti-Cancer Drug Res. 1991, 6, 501. [Google Scholar]
  2. Emmons, W. D. The oxidation of amines with peracetic acid. J. Am. Chem. Soc. 1957, 79, 5528. [Google Scholar] [CrossRef]
  3. Gilbert K., E.; Borden, W. T. Peracid oxidation of aliphatic amines: general synthesis of nitroalkanes. J. Org. Chem. 1979, 44, 659. [Google Scholar] [CrossRef]
Sample Availability: Available from the authors.

Share and Cite

MDPI and ACS Style

Baraldi, P.G.; Cacciari, B.; Romagnoli, R.; Spalluto, G. 1-Methyl-3-nitro-5-methoxycarbonyl Pyrazole. Molecules 1998, 3, M46. https://doi.org/10.3390/M46

AMA Style

Baraldi PG, Cacciari B, Romagnoli R, Spalluto G. 1-Methyl-3-nitro-5-methoxycarbonyl Pyrazole. Molecules. 1998; 3(2):M46. https://doi.org/10.3390/M46

Chicago/Turabian Style

Baraldi, Pier Giovanni, Barbara Cacciari, Romeo Romagnoli, and Giampiero Spalluto. 1998. "1-Methyl-3-nitro-5-methoxycarbonyl Pyrazole" Molecules 3, no. 2: M46. https://doi.org/10.3390/M46

Article Metrics

Back to TopTop