Rapid, efficient and selective reduction of aromatic nitro compounds with sodium borohydride and Raney nickel

被引:118
作者
Pogorelic, Ivan [1 ]
Filipan-Litvic, Mirela [1 ]
Merkas, Sonja [1 ]
Ljubic, Goranka [1 ]
Cepanec, Ivica [1 ]
Litvic, Mladen [1 ]
机构
[1] BELUPO Pharmaceut Inc, R&D, CRO-10000 Zagreb, Croatia
关键词
reduction; nitro group; aromatic amines; Raney nickel; sodium borohydride;
D O I
10.1016/j.molcata.2007.05.020
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A new efficient, mild and practical method for reduction of aromatic nitro compounds employing NaBH4/Raney nickel system is reported. The method is simple, inexpensive, easily scaled-up and applicable for large scale preparation of different substituted anilines as well as other heterocyclic aryl amines. (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:202 / 207
页数:6
相关论文
共 52 条
[41]   Reduction of carbonyl compounds to alcohols using ferric chloride-zinc-dimethylformamide-water system [J].
Sadavarte, VS ;
Swami, SS ;
Desai, DG .
SYNTHETIC COMMUNICATIONS, 1998, 28 (07) :1139-1142
[42]  
SAFRONOVA LA, 1999, J GEN CHEM USSR, V69, P917
[43]   Ultrasound-promoted highly chemoselective reduction of aromatic nitro compounds to the corresponding N-arylhydroxylamines using zinc and HCOONH4 in CH3CN [J].
Shi, QX ;
Lu, RW ;
Jin, K ;
Zhang, ZX ;
Zhao, D .
CHEMISTRY LETTERS, 2006, 35 (02) :226-227
[44]  
Srinivasa GR, 2003, INDIAN J CHEM B, V42, P2882
[45]   SYNTHESIS OF CYCLOPROP[C]INDOL-5-ONES FROM 4-DIAZO-3-[N-(2-PROPENYL)AMIDO]CYCLOHEXADIEN-1-ONES - EXPLORATION OF COPPER(I) AND COPPER(II) COMPLEXES AS CATALYSTS [J].
SUNDBERG, RJ ;
PITTS, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :3048-3054
[46]   Solvent-free reduction of aromatic nitro compounds with alumina-supported hydrazine under microwave irradiation [J].
Vass, A ;
Dudás, J ;
Tóth, J ;
Varma, RS .
TETRAHEDRON LETTERS, 2001, 42 (32) :5347-5349
[47]   4-amino-1-methylbenzimidazole [J].
Viktor, M ;
Ilavsky, D ;
Salon, J .
MOLECULES, 1997, 2 (05) :M13-+
[48]   Chemoselective reductions of nitroarenes:: bromoethanol-assisted phthalocyanatoiron/NaBH4 reductions [J].
Wilkinson, HS ;
Tanoury, GJ ;
Wald, SA ;
Senanayake, CH .
TETRAHEDRON LETTERS, 2001, 42 (02) :167-170
[49]   Liquid-liquid-liquid phase transfer catalysis: A novel and green concept for selective reduction of substituted nitroaromatics [J].
Yadav, GD ;
Lande, SV .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) :1235-1241
[50]   Convenient reduction of nitrobenzenes to anilines using electrochemically generated nickel [J].
Yasuhara, A ;
Kasano, A ;
Sakamoto, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2301-2303