Synlett 2018; 29(17): 2257-2264
DOI: 10.1055/s-0037-1610658
letter
© Georg Thieme Verlag Stuttgart · New York

Fe(ClO4)3·H2O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles

Chengliang Feng
a   Institute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China   Email: fcl085620@163.com
,
Bin Yan
a   Institute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China   Email: fcl085620@163.com
,
Guibo Yin
a   Institute of Pharmaceutical Engineering, Jiangsu College of Engineering and Technology, Nantong, Jiangsu 226000, P. R. of China   Email: fcl085620@163.com
,
Junqing Chen
b   School of Biological Sciences & Medical Engineering, Southeast University, Nanjing, Jiangsu 211189, P. R. of China
,
Min Ji*
b   School of Biological Sciences & Medical Engineering, Southeast University, Nanjing, Jiangsu 211189, P. R. of China
› Author Affiliations
The financial support for this work was provided by Nantong City Science Foundation (No. 2015) and the Science Program of Jiangsu College of Engineering and Technology.
Further Information

Publication History

Received: 06 June 2018

Accepted after revision: 24 August 2018

Publication Date:
26 September 2018 (online)


Abstract

An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO4)3·H2O is described. Fe(ClO4)3·H2O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.

Supporting Information

 
  • References and Notes

  • 1 Singh GS. Tetrahedron 2003; 59: 7631
  • 2 Allen CL. Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
  • 3 Valeur E. Bradley M. Chem. Soc. Rev. 2009; 38: 606
    • 4a Saxo E. Bertozzi CZ. Science 2000; 287: 2007
    • 4b Damkaci F. De Shong P. J. Am. Chem. Soc. 2003; 125: 4408
    • 4c Gololobov YG. Kasukhin LF. Tetrahedron 1992; 48: 1353
    • 5a Ribelin T. Katz CE. English DG. Smith S. Manukyan AK. Day VW. Neuenswander B. Poutsma JL. Aube J. Angew. Chem. Int. Ed. 2008; 47: 6233
    • 5b Lang S. Murphy JA. Chem. Soc. Rev. 2006; 35: 146
    • 6a Owston NA. Parker AJ. Williams JM. J. Org. Lett. 2007; 9: 3599
    • 6b Hashimoto M. Obora Y. Sakaguchi S. Ishii Y. J. Org. Chem. 2008; 73: 2894
    • 7a Chang JW. W. Ton TM. U. Tania S. Taylor PC. Chan PW. H. Chem. Commun. 2010; 46: 922
    • 7b Ton TM. U. Tejo C. Tania S. Chang JW. W. Chan PW. H. J. Org. Chem. 2011; 76: 4894
    • 7c Ghosh SC. Ngiam JS. Y. Chai CL. L. Seayad AM. Dang TT. Chen A. Adv. Synth. Catal. 2012; 354: 1407
    • 7d Ghosh SC. Ngiam JS. Y. Seayad AM. Tuan DT. Chai CL. L. Chen A. J. Org. Chem. 2012; 77: 8007
    • 7e Goh KS. Tan C.-H. RSC Adv. 2012; 2: 5536
    • 7f Liu X. Jensen KF. Green Chem. 2012; 14: 1471
    • 7g Li G.-L. Kung KK.-Y. Wong M.-K. Chem. Commun. 2012; 48: 4112
    • 7h Zhu M. Fujita K.-i. Yamaguchi R. J. Org. Chem. 2012; 77: 9102
    • 7i Krabbe SW. Chan VS. Franczyk TS. Shekhar S. Napolitano J. Presto CA. Simanis JA. J. Org. Chem. 2016; 81: 10688
  • 8 Jiang D. -H. He T. Ma L. Wang Z.-Y. RSC Adv. 2014; 4: 64936
  • 9 Firouzabadi H. Sardarian AR. Badparva H. Synth. Commun. 1994; 24: 601
  • 10 Barbero M. Bazzi S. Cadamuro S. Dughera S. Eur. J. Org. Chem. 2009; 430
  • 11 Theerthagiri P. Lalitha A. Arunachalam PN. Tetrahedron Lett. 2010; 51: 2813
  • 12 Anxionnat B. Guérinot A. Reymond S. Cossy J. Tetrahedron Lett. 2009; 50: 3470
  • 13 Mukhopadhyay M. Reddy MM. Maikap GC. Iqbal J. J. Org. Chem. 1995; 60: 2670
  • 14 Lakouraj MM. Movassagh B. Fasihi J. Synth. Commun. 2000; 30: 821
  • 15 Sanz R. Martínez A. Guilarte V. Álvarez-Gutiérrez JM. Rodríguez F. Eur. J. Org. Chem. 2007; 4642
  • 16 Shakeri MS. Tajik H. Niknam K. J. Chem. Sci. 2012; 124: 1025
  • 17 Karimian E. Akhlaghinia B. Ghodsinia SS. E. J. Chem. Sci. 2016; 128: 429
  • 18 Posevins D. Suta K. Turks M. Eur. J. Org. Chem. 2016; 1414
  • 19 Katkar KV. Chaudhari PS. Akamanchi KG. Green Chem. 2011; 13: 835
  • 20 Khalafi-Nezhad A. Foroughi HO. Doroodmandab MM. Panahi F. J. Mater. Chem. 2011; 21: 12842
  • 21 Zhao X.-N. Hu H.-C. Zhang F.-J. Zhang Z.-H. Appl. Catal. A.: Gen. 2014; 482: 258
  • 22 Khaksar S. Fattahi E. Fattahi E. Tetrahedron Lett. 2011; 52: 5943
  • 23 Qu G.-R. Song Y.-W. Niu H.-Y. Guo H.-M. John S.-F. RSC Adv. 2012; 2: 6161
  • 24 Mokhtary M. Najafizadeh F. E-J. Chem. 2012; 9: 576
  • 25 Mokhtary M. Goodarzi G. Chin. Chem. Lett. 2012; 23: 293
  • 26 Tamaddon F. Tavakoli F. J. Mol. Catal. A.: Chem. 2011; 337: 52
  • 27 Baum JC. Milne JE. Murry JA. Thiel OR. J. Org. Chem. 2009; 74: 2207
  • 28 Nasr-Esfahani M. Montazerozohori M. Karami Z. Org. Prep. Proced. Int. 2016; 48: 321
  • 29 Hanzawa Y. Kasashima Y. Tomono K. Mino T. Sakamoto M. Fujita T. J. Oleo. Sci. 2012; 61: 393
  • 30 Typical Experimental Procedure for the Reaction of Benzonitrile and Esters (Benzyl, sec-Alkyl and Primary Alkyl Esters) A mixture of benzonitrile (5 mmol), benzyl acetate (6 mmol), and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added, and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 mL), dried with anhydrous Na2SO4, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder a (0.91 g, 87% yield). Compound a 1H NMR (CDCl3, 400 MHz): δ = 7.80 (m, 2 H), 7.78–7.25 (m, 8 H), 6.51 (s, 1 H), 4.64 (d, J = 5.8 Hz, 2 H) ppm. 13C NMR (CDCl3, 100 MHz): δ = 167.4, 138.2, 134.4, 131.6, 128.8, 128.6, 127.9, 127.6, 127.0, 44.1 ppm.
  • 31 Typical Experimental Procedure for the Reaction of Various Nitriles and Acetic Esters A mixture of 3-methylbenzonitrile (5 mmol), benzyl acetate (6 mmol), and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added, and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 mL), dried with anhydrous Na2SO4, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder n (0.96 g, 86% yield). Compound n 1H NMR (CDCl3, 400 MHz): δ = 7.61–7.55 (m, 2 H), 7.34–7.28 (m, 7 H), 6.55 (s, 1 H), 4.62 (d, J = 5.64 Hz, 2 H), 2.37 (s, 3 H) ppm. 13C NMR (CDCl3, 100 MHz): δ = 167.6, 138.4, 138.3, 134.3, 132.3, 128.8, 128.4, 127.9, 127.7, 127.6, 123.9, 44.1, 21.3 ppm.
  • 32 Typical Experimental Procedure for the Reaction of Nitriles and di-tert-Butyl Malonate A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), di-tert-butyl malonate (3 mmol), and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomed flask. Then, the reaction mixture was heated at 80 °C for 5 h. After completion of the reaction monitored by thin layer chromatography (TLC), water (10 mL) was added and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The organic layers were collected, combined, washed with water (3 × 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure product was obtained by directly passing through a silica gel (200–300 mesh) column to give a white powder 1m (1.08 g, 84% yield). Compound 1m 1H NMR (400 MHz, CDCl3): δ = 7.41–7.35 (m, 2 H), 7.12–7.10 (m, 1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6, 51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C12H15Cl2NO [M + H]+: 259.0531; found: 259.0533.