Skip to main content
SpringerLink
Log in

Hydroxylamine on Clay: a Direct Synthesis of Nitriles from Aromatic Aldehydes Using Microwaves Under Solvent-Free Conditions

  • Note
  • Published:
Molecules Online

Abstract

In a solvent-free system, hydroxylamine hydrochloride impregnated montmorillonite K 10 clay expeditiously converts arylaldehydes to the corresponding nitriles under microwave irradiation conditions. This rapid one-pot method produces pure products in high yields (89–95%) within 1 to 1.5 min.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. (a) Fizet C, Streith J (1974) Tetrahedron Lett 3187; (b) Miller M, Loudon G (1975) J Org Chem 40:126; (c) Sosnovsky G, Krogh JA, Umhoefer SG (1979) Synthesis 722; (d) Olah GA, Keuni T (1979) Synthesis 112; (e) Friedrich K, Wallensfels K (1970) In: Rappoport Z (ed) The chemistry of cyano groups. Wiley-Interscience, NewYork

  2. (a) Mowry DT (1948) Chem Rev 42:250; (b) Pomeroy JH, Craig CA (1959) J Am Chem Soc 81:6340; (c) Foley PJ (1969) J Org Chem 34:2805; (d) Clive DL (1970) J Chem Soc Chem Commun 1014; (e) Dauzonne D, Demerseman P, Royer R (1981) Synthesis 739; (f) Karmarkar SN, Kelkar SL (1985) Wadia Synthesis 510; (g) Villemin D, Lalaoui M, Ben Album D (1991) Chem and Ind 176; (h) Delgado F, Cano AC, Garcia O, Alvarado J, Velasco L, Alvarez C, Rudler H (1992) Synth Commun 22:2125; (f) Lehnert W (1971) Tetrahedron Lett 6:559; (g) Rosini G, Baccolini G, Cacchi S (1973) J Org Chem 38:1060; (h) Foley HG, Dalton DR (1973) J Chem Soc Chem Commun 628; (i) Bandgar BP, Jagtap SR, Ghodeshwar SB, Wadgaonkar PP (1995) Synth Commun 25:2993; (j) Sampath Kumar HM, Mohanty PK, Suresh Kumar M, Yadav JS (1997) Synth Commun 27:1327

  3. Meshram HM (1992) Synthesis 943

  4. Narayan Rao M, Kumar P, Garyaki K (1989) Org Prep Proceed Int 21:230

  5. (a) McKillop A, Young DW (1979) Synthesis 401, 481; (b) Laszlo P (1987) Preparative chemistry using supported reagents. Academic Press, San Diego; (c) Clark JH (1994) Catalysis of organic reactions by supported inorganic reagents. VCH, NewYork

  6. For recent reviews on microwave-assisted chemical reactions see: (a) Abramovich RA (1991) Org Prep ProcedInt 23:683; (b) Whittaker AG, Mingos DMP (1994) J Microwave Power Electromagn Energy 29:195; (c) Majetich G, Hicks R (1995) J Microwave Power Electromagn Energy 30:27; (d) Caddick S (1995) Tetrahedron 51:10,403; (e) Bose AK, Banik BK, Lavlinskaia N, Jayaraman M, Manhas MS (1997) Chemtech 27:18; (f) Varma R S (1997) Microwave-assisted reactions under solvent-free dry conditions. In: Clark DE, Sutton WH, Lewis DA (eds) Microwaves: theory and application in material processing IV. American Ceramic Society, Ceramic Transactions, pp 375-365

  7. (a) Oussaid A, Thach LN, Loupy A (1997) Tetrahedron Lett 38:2451; (b) Villemin D, Benalloum A (1991) Synth Commun 21:1, 63; (c) Lerestif JM, Toupet L, Sinbandhit S, Tonnard F, Bazureau JP, Hamelin J (1997) Tetrahedron 53:6351

  8. For cleavage-deprotection reactions see: (a) Varma RS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:3207; (b) Varma RS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:4603; (c) Varma RS, Varma M, Chatterjee AK (1993) J Chem Soc Perkin Trans 1 999; (d) Varma RS, Lamture JB, Varma M (1993) Tetrahedron Lett 34:3029; (e) Varma RS, Saini RK (1997) Tetrahedron Lett 38:2623; (f) Varma RS, Meshram HM (1997) Tetrahedron Lett 38:5427; (g) Varma RS, Meshram HM (1997) Tetrahedron Lett 38:7973; (h) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:8819 For condensation-cyclization reactions see: (i) Varma RS, Dahiya R, Kumar S (1997) Tetrahedron Lett 38:2039; (j) Varma RS, Dahiya R (1997) Synlett 1245; (k) Varma RS, Dahiya R, Kumar S (1997) Tetrahedron Lett 38:5131; (l) Varma RS, Saini RK (1997) Synlett 857 For oxidation reactions see: (m) Varma RS, Dahiya R (1997) Tetrahedron Lett 38:2043; (n) Varma RS, Saini RK, Meshram HM (1997) Tetrahedron Lett 38:6525; (o) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:7029; (p) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:7823; (q) Varma RS, Dahiya R (1998) Tetrahedron Lett 39:1307; (r) Varma RS, Saini RK (1998) Tetrahedron Lett 39:1481 For reductions see: (s) Varma RS, Saini RK (1997) Tetrahedron Lett 38:4337

  9. (a) CRC hand book of data on organic compounds (1998). CRC Press, Boca Raton, Florida; (b) Hand book of tables for organic compounds identification, 3rd edn (1978). Chemical Rubber Company, Cleveland, Ohio

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Sam Houston State University, TX 77341-2117, Huntsville, USA

    Rajender S. Varma & Kannan P. Naicker

  2. Texas Research Institute for Environmental Studies (TRIES), Sam Houston State University, TX 77341-2117, Huntsville, USA

    Rajender S. Varma

Authors
  1. Rajender S. Varma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kannan P. Naicker
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rajender S. Varma.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Varma, R.S., Naicker, K.P. Hydroxylamine on Clay: a Direct Synthesis of Nitriles from Aromatic Aldehydes Using Microwaves Under Solvent-Free Conditions. Molecules Online 2, 94–96 (1998). https://doi.org/10.1007/s007830050061

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s007830050061

Search

Navigation