Synthesis of a novel Schiff base {3,4-Bis[(2-Hydroxy-benzylidene) amino] phenyl} phenyl methanone

A. A. jarrahpour*, M. Zarei

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran Tel. No. 0098 711 2284822,  Fax: 0098 711 2280926, E-mail: [email protected],  [email protected]

Received: 7 August 2003 / Accepted: 18 September 2003 / Published: 24 February 2004

              1                   2                                           3

A mixture of (3,4-diaminophenyl) phenyl methanone 1 (2.12 g, 10.00 mmol), 2-hydroxybenzaldehyde 2 (2.44 g, 20.00 mmol) and sodium sulfate (5.00 g) in dry dichloromethane (50.00 ml) was stirred at room temperature for five hours.  The suspension was filtered and washed with dichlormethane. The solvent was evaporated and compound 3 was formed as an orange solid which was recrystalized from ethanol (3.41 g, 81.30%).

 m.p. 159-161^oC. 

IR (KBr) (cm^-1): 1600 (C=N), 1650 (CO), 3100-3300 (OH)

 ¹H-NMR (CDCl₃) (250 MHz)(ppm): 6.95-7.76 (16H, m, 4Ph), 8.59 (2H, s, N=CH), 12.71 (2H, br, OH)

 ¹³C-NMR (CDCl₃) (62.90 MHz)(ppm): 115.00-144.25 (aromatic carbons), 159.45 (C-OH), 163.05 (C=N), 193.00 (CO).

MS (m/z, %): 420 (M ⁺, 8.40), 314 ( PhCOPh(N)(N=CHPhOH, 100.00), 237 (PhCOPh(N=CH)₂, 70.00) , 209 (PhCOPh(N)₂, 23.50 ), 182 (PhCOPh, 5.00), 105 (PhCO, 41.20), 77 (PhH)

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 81-SC-1540-C220 ).

Sample availability: Available from MDPI
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