Highly Convenient, One-Pot Synthesis of Nitriles from Aldehydes Using the NH₂OH·HCl/NaI/MeCN System

Abstract

Direct transformation of both aliphatic and aromatic aldehydes to the corresponding nitriles, can be easily performed by the reaction of an aldehyde with a slight excess of hydroxylamine hydrochloride, in refluxing acetonitrile and in the presence of 0.5 equivalents of sodium iodide as catalyst.

Key words

aldehydes - hydroxylamine hydrochloride - sodium iodide - catalysis - nitriles

References

• 1a Chichiro M. Nagamoto H. Takemura I. Kitano K. Komatsu H. Sekiguchi K. Tabusa F. Mori T. Tomonnaga M. Yabuuchi Y. J. Med. Chem.  1995,  38:  353 
• 1b Serrano JL. Sierra T. Gonzales Y. Bolm C. Weickhardt K. Magnus A. Moll G. J. Am. Chem. Soc.  1995,  117:  8321 
• 1c Diana GD. Cutcliffe D. Volkots DL. Mallamo JP. Bailey TR. Velico N. Oglesby RC. Nitz TJ. Wetzel J. Giranda V. Pevear DC. Dutko FJ. J. Med. Chem.  1993,  36:  3240 
• 1d Khanna IK. Weier RM. Yu Y. Xu XD. Koszyk FJ. Collins PW. Koboldt CM. Veenhuizen AW. Perkins WE. Casler JJ. Masferrer JL. Zhang YY. Gregory SA. Seibert K. Isakson PC. J. Med. Chem.  1997,  40:  1634 
• 1e Medwid JB. Paul R. Baker JS. Brockman JA. Du MT. Hallet WA. Hanfin JW. Hardy RA. Tarrant ME. Torley IM. Wrenn S. J. Med. Chem.  1990,  26:  4351 
• 1f Judkins BD. Allen DG. Cook TA. Evans B. Sardharwala TE. Synth. Commun.  1996,  26:  4351 
• 2a March J. Advanced Organic Chemistry   Wiley; New York: 1992.  p.907 
• 2b Corey EJ. Cheng XM. The Logic of Chemical Synthesis   Wiley; New York: 1989. 
• 2c Ho TL. Tactics of Synthesis   Wiley; New York: 1994. 
• 2d Cohen MA. Sawden J. Turner NJ. Tetrahedron Lett.  1990,  31:  7223 
• 2e Yamada H. Chimia  1993,  47:  69 
• 2f Crosby J. Moiller J. Parratt JS. Turner NJ. J. Chem. Soc., Perkin Trans. 1  1994,  1679 
• 2g Luo F.-T. Jeevanandam A. Tetrahedron Lett.  1998,  39:  9455 
• 3a Cohen MA. Sawden J. Turner NJ. Tetrahedron Lett.  1990,  31:  7223 
• 3b Yamada H. Chimia  1993,  47:  69 
• 3c Luo F.-T. Jeevanandam A. Tetrahedron Lett.  1998,  39:  9455 
• 3d Bandgar BP. Jagtap SR. Ghodeshwar SB. Wadgaonkar PP. Synth. Commun.  1995,  25:  2993 
• 3e Miller CP. Kaufman DH. Synlett  2000,  1169 
• 3f Lingaiah N. Narender R. Synth. Commun.  2002,  32:  2391 
• 3g Iranpoor N. Firouzabadi H. Aghapour G. Synth. Commun.  2002,  32:  2535 
• 4a Wang E.-C. Lin G.-J. Tetrahedron Lett.  1998,  36:  4047 
• 4b Kamal A. Arifuddin M. Rao NV. Synth. Commun.  1998,  28:  4507 
• 4c Webb KS. Levy D. Tetrahedron Lett.  1995,  36:  5117 
• 4d Ali SL. Nikalje MD. Dewkar GK. Paraskar AS. Nikale MD. Sudalai A. J. Chem. Res., Synop.  2000,  30 
• 4e Chakraborti AK. Kaur G. Tetrahedron  1999,  55:  13265 
• 4f Das B. Ramesh C. Madhusudham P. Synlett  2000,  1599 
• 4g Sharghi H. Sarvari MH. Tetrahedron  2002,  58:  10323 
• 4h Boruah M. Konwar D. J. Org. Chem.  2002,  67:  7138 
• 4i Srinivas KVNS. Reddy BE. Das B. Synlett  2002,  625 
• 4j Sharghi H. Sarvari MH. Synthesis  2003,  243