A Green Microwave Assisted Synthesis of New Anthracene Derivatives as an Environmentally Friendly Alternatives
Krishna k.Ranawat1*, Sadhana Singh2, G.P. Singh1, Rachana Gupta1, Vinod Bhatt1
1Department of Chemistry, B.N.P.G. College, Udaipur- (Raj.),INDIA
2Department of Chemistry, S.B.P. Govt. College, Dungarpur -(Raj.),INDIA
ABSTRACT:
Synthesis of polynuclear aromatic hydrocarbons and its derivatives was carried under microwave irradiations. The title compound, (anthracene-9-yl) methylamine, was synthesized in high yield by reaction of 9-chloromethylanthracene and The structure of this new compound was confirmed by elemental analysis,IR,Mass,1H NMR spectral data.
KEYWORDS: 9-chloromethyl anthracene, piperidine, microwave irradiation, mass, nm.
A considerable amount of research has been devoted to the synthesis of( anthracene-9-yl )methylamines used in many synthetic routes[1].In 1986,Gedye et al.[2,3] and Giguere et.al.[4,6] demonstrated that a wide variety of organic reaction can be conducted very rapidly using microwave irradiation. Since then, several other groups have described accelerated organic reaction [7-9] Additionally some recently reported example include one pot reaction[10]and particular organic reactions such as Suzuki couplings[11], claisen rearrengement [12] ,but no study of the microwave assisted synthesis of (anthracene-9-yl)methylamines has been reported. We wish to report herein a facile high yielding synthesis of this compound in a short time using a domestic microwave oven.
EXPERIMENTAL:
Compounds prepared by a new microwave irradiated method. In this method 9-chloromethylanthracene, piperidine and DMSO was mixes in 150 ml beaker and irradiated in microwave oven. After 13 min., the reaction mixture was poured into water and extracted with diethyl ether to remove side product. The organic layer was separated, washed with water and dried over Na2SO4 and the solid obtained was recrystallised. Then the product subjected to analysis for their melting point, TLC etc.
RESULT AND DISCUSSION:
Synthesis of compound was carried out in single pot domestic oven. The product formed was confirmed through TLC and by spectral studies. Formation of compound followed the reaction pathway as shown in reaction scheme;
Elemental analysis (%) C 87.24, H 7.67, N 5.09
1H NMR δ1.52-1.76 (6H, m), 2.60-2.82 (4H, m), 4.54 (2H, s), 7.52-8.59 (9H, m, aromatic)
MS, m/z 275 (M+)
ACKNOWLEDGEMENT:
The authors are grateful to Dept. of Chemistry, B.N.P.G. College for providing the experimental facilities and CDRI Luck now for spectral analysis.
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Received on 18.08.2014 Modified on 09.09.2014
Accepted on 10.09.2014 © AJRC All right reserved
Asian J. Research Chem. 7(9): September 2014; Page 799-800