Skip to main content

An efficient and convenient synthesis of N-substituted amides under heterogeneous condition using Al(HSO4)3 via Ritter reaction

Journal of Chemical Sciences volume 128, pages 429–439 (2016)Cite this article

Abstract

An efficient and inexpensive synthesis of N-substituted amides from the reaction of aliphatic and aromatic nitriles with various benzylic alcohols (secondary and tertiary) and tert-butyl alcohol by refluxing nitromethane via the Ritter reaction catalyzed by aluminum hydrogen sulfate [Al(HSO4)3] is described. The catalyst which is an air-stable, cost-effective solid acid could be readily recycled by filtration and reused four times without any significant loss of its activity.

An efficient and inexpensive synthesis of N-substituted amides by refluxing nitromethane via the Ritter reaction catalyzed by aluminum hydrogen sulfate [Al(HSO4)3] is described. The catalyst which is an air-stable, cost-effective solid acid could be readily recycled by filtration and reused four times without any significant loss of its activity.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price includes VAT (USA)
Tax calculation will be finalised during checkout.

Scheme 1
Scheme 2

References

  1. (a) Ritter J J and Minieri P P 1948 J. Am. Chem. Soc. 70 4045; (b) Benson F R and Ritter J J 1949 J. Am. Chem. Soc. 71 4128; (c) Krimen L I and Cota D J 1969 Org. React. 17 213

  2. Brewer A R E 2007 In Name Reactions for Functional Group Transformations Li J J and Corey E J (Ed.) (John Wiley & Sons: Hoboken) p. 471

  3. Olah G A, Yamato T, Iyer P S, Trivedi N J, Singh B P and Surya Prakash G K 1987 Mater. Chem. Phys. 17 21

    CAS  Article  Google Scholar 

  4. Yamato T, Hu J Y and Shinoda N 2007 J. Chem. Res. 11 641

    Article  Google Scholar 

  5. Polshettiwar V and Varma R S 2008 Tetrahedron Lett. 49 2661

    CAS  Article  Google Scholar 

  6. Gullickson G C and Lewis D E 2003 Synthesis 681

  7. Subba Reddy B V, Sivasankar Reddy N, Madan C. and Yadav J S 2010 Tetrahedron Lett. 51 4827

    CAS  Article  Google Scholar 

  8. Sanz R, Martínez A, Guilarte V, Álvarez-Gutiérrez J M and Rodríguez F 2007 Eur. J. Org. Chem. 2007 4642

    Article  Google Scholar 

  9. Ma’mani L, Heydari A and Sheykhan M 2010 Appl. Catal. A. 384 122

    Article  Google Scholar 

  10. Mohammadi Ziarani G., Badiei A R, Dashtianeh Z, Gholamzadeh P and Mohtasham N 2013 Res. Chem. Intermed. 39 3157

    CAS  Article  Google Scholar 

  11. Tamaddon F, Khoobi M and Keshavarz E 2007 Tetrahedron Lett. 48 3643

    CAS  Article  Google Scholar 

  12. Aoyama T, Kobayashi T, Takido T and Kodomari M 2014 Synlett 25 2365

    Article  Google Scholar 

  13. Rapolu R K, Naba Mukul B, Bommineni S R, Potham R, Mulakayala N and Oruganti S 2013 RSC Adv. 3 5332

    CAS  Article  Google Scholar 

  14. Norell J R 1970 J. Org. Chem. 35 1611

    CAS  Article  Google Scholar 

  15. Chen H G, Goel O P, Kesten S and Knobelsdorf J 1996 Tetrahedron Lett. 45 8129

    Article  Google Scholar 

  16. Baum J C, Milne J E, Murry J A and Thiel O R 2009 J. Org. Chem. 74 2207

    CAS  Article  Google Scholar 

  17. Martinez A G, Alvarez R M, Vilar E T, Fraile A G, Hanack M and Subramanian L R 1989 Tetrahedron Lett. 30 581

    Article  Google Scholar 

  18. Khaksar S and Fattahi E 2011 Tetrahedron Lett. 52 5943

    CAS  Article  Google Scholar 

  19. Jiang S, Wang Z, Jiang Z, Li J, Zhou S and Pu L 2012 Lett. Org. Chem. 9 24

    CAS  Article  Google Scholar 

  20. Callens E, Burton A J and Barrett A G M 2006 Tetrahedron Lett. 47 8699

    CAS  Article  Google Scholar 

  21. Theerthagiri P, Lalitha A and Arunachalam P N 2010 Tetrahedron Lett. 51 2813

    CAS  Article  Google Scholar 

  22. Yaragorla S, Singh G, Saini P L and Reddy M K 2014 Tetrahedron Lett. 55 4657

    CAS  Article  Google Scholar 

  23. Al-huniti M H and Lepore S D 2013 Adv. Synth. Catal. 355 3071

    CAS  Article  Google Scholar 

  24. (a) Top S and Jaouen G 1981 J. Org. Chem. 46 78; (b) Barton D H R, Magnus P D and Young R N 1973 J. Chem. Soc., Chem. Commun. 331; (c) Mukhopadhyay M, Reddy M M, Maikap G G and Iqbal J 1995 J. Org. Chem. 60 2670

  25. Kalkhambkar R G, Waters S N and Laali K K 2011 Tetrahedron Lett. 52 867

    CAS  Article  Google Scholar 

  26. Jiang F, Lin Y J, Duan H F, Li Z H, Cao J G and Liang D P 2010 Chem. Res. Chin. Univ. 26 384

    CAS  Google Scholar 

  27. Olah G A, Balaram Gupta B G and Narang S C 1979 Synthesis 274

  28. Ibrahim N, Hashmi A S K and Rominger F 2011 Adv. Synth. Catal. 353 461

    CAS  Article  Google Scholar 

  29. Shakeri M S, Tajik H and Niknam K. 2012 J. Chem. Sci. 124 1025

    CAS  Article  Google Scholar 

  30. Gawande M B, Rathi A K, Nogueira I D, Varma R S and Branco P S 2013 Green Chem. 15 1895

    CAS  Article  Google Scholar 

  31. Mokhtary M and Goodarzi G 2012 Chin. Chem. Lett. 23 293

    CAS  Article  Google Scholar 

  32. Niknam K, Zolfigol M A and Sadabadi T 2007 J. Iran. Chem. Soc. 4 199

    CAS  Article  Google Scholar 

  33. Sadeghi B, Farahzadi E and Hassanabadi A 2012 J. Chem. Res. 36 539

    CAS  Article  Google Scholar 

  34. Dokli I and Gredičak M 2015 Eur. J. Org. Chem. 2015 2727

    CAS  Article  Google Scholar 

  35. Barbero M, Bazzi S, Cadamuro S and Dughera S 2009 Eur. J. Org. Chem. 2009 430

    Article  Google Scholar 

  36. Katkar K V, Chaudhari P S and Akamanchi K G 2011 Green Chem. 13 835

    CAS  Article  Google Scholar 

  37. Jefferies L R and Cook S P 2014 Tetrahedron Lett. 70 4204

    CAS  Article  Google Scholar 

  38. Salehi P and Rostamian M A 2000 Synth. Commun. 30 671

    CAS  Article  Google Scholar 

  39. Maki T, Ishihara K and Yamamoto H 2006 Org. Lett. 8 1431

    CAS  Article  Google Scholar 

  40. Maki T, Ishihara K and Yamamoto H 2007 Tetrahedron 63 8645

    CAS  Article  Google Scholar 

  41. Niknam K., Zolfigol M A, Shayeghb M and Zareb R 2007 J. Chin. Chem. Soc. 54 1067

    CAS  Article  Google Scholar 

  42. Xufeng L, Wang J, Fangxi X and Yanguang W 2009 J. Chem. Res. 10 638

    Google Scholar 

  43. Bakibaev A A, Tignibidina L G, Filimonov V D, Pustovoitov A V, Gorshkova V K, Saratikov A S and Krasnov V A 1989 Pharm. Chem. J. 23 978

    Article  Google Scholar 

  44. Hazarikaa N, Baishya G and Phukan P 2015 Synthesis 47 2851

    Article  Google Scholar 

  45. Khalafi-Nezhad A, Foroughi H O, Doroodmand M M and Panahi F 2011 J. Mater. Chem. 21 12842

    CAS  Article  Google Scholar 

  46. Salehi P, Khodaei M M, Zolfigol M A and Keyvan A 2001 Synth. Commun. 31 1947

    CAS  Article  Google Scholar 

  47. Agwada V C 1984 J. Chem. Eng. Data. 29 231

    CAS  Article  Google Scholar 

  48. Lasslo A and Jordan W D 1956 J. Org. Chem. 21 805

    CAS  Article  Google Scholar 

  49. Weibin S, Lei M and Lihong H 2011 Synth. Commun. 41 3186

    Article  Google Scholar 

  50. Martinelli J R, Clark T P, Watson D A, Munday R H and Buchwald S L 2007 Angew. Chem. Int. Ed. 46 8460

    CAS  Article  Google Scholar 

  51. Zhang M, Imm S, Baehn S, Neubert L, Neumann H and Beller M 2012 Angew. Chem. Int. Ed. 51 3905

    CAS  Article  Google Scholar 

  52. Debnath P, Baeten M, Lefvre N, Van Daele S and Maes B U W 2015 Adv. Synth. Catal. 357 197

    CAS  Article  Google Scholar 

  53. Sanguigni J A and Levine R 1964 J. Med. Chem. 7 573

    CAS  Article  Google Scholar 

  54. Neale R S, Marcus N L and Schepers R G 1966 J. Am. Chem. Soc. 88 3051

    CAS  Article  Google Scholar 

  55. Khafajeh S, Akhlaghinia B, Rezazadeh S and Eshghi H 2014 J. Chem. Sci. 126 1903

    CAS  Article  Google Scholar 

  56. NazariMoghadam B, Akhlaghinia B and Rezazadeh S 2015 Res. Chem. Intermed. DOI: 10.1007/s11164-015-2098-y

  57. (a) Razavi N and Akhlaghinia B 2015 RSC Adv. 5 12372; (b) Razavi N and Akhlaghinia B 2016 New J. Chem. 40 447; (c) Zarghani M and Akhlaghinia B 2015 Appl. Organometal. Chem. 29 683; (d) Zarghani M and Akhlaghinia B 2015 RSC Adv. 5 87769; (e) Ghodsinia E S S and Akhlaghinia B 2015 RSC Adv. 5 49849; (f) Zareie Z and Akhlaghinia B 2015 Chem. Pap. 69 1421; (j) Jahanshahi R and Akhlaghinia B 2015 RSC Adv. 5 104087

Download references

Acknowledgements

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council (Grant no. p/ 3/33741).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad, 9177948974, Iran

    ELNAZ KARIMIAN, BATOOL AKHLAGHINIA & SARA S E GHODSINIA

Authors
  1. ELNAZ KARIMIAN
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. BATOOL AKHLAGHINIA
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. SARA S E GHODSINIA
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to BATOOL AKHLAGHINIA.

Additional information

Supplementary Information (SI)

Supplementary Information is available at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOCX 19.8 MB)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

KARIMIAN, E., AKHLAGHINIA, B. & E GHODSINIA, S.S. An efficient and convenient synthesis of N-substituted amides under heterogeneous condition using Al(HSO4)3 via Ritter reaction. J Chem Sci 128, 429–439 (2016). https://doi.org/10.1007/s12039-016-1036-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-016-1036-x

Keywords

  • Aluminum hydrogen sulfate [Al(HSO4)3]
  • Ritter reaction
  • N-substituted amides
  • heterogeneous catalyst
  • nitriles
  • alcohols.