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

Jarrahpour, A. A.; Zarei, M.

doi:10.3390/M353

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

by

A. A. Jarrahpour

^* and

M. Zarei

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

^*

Author to whom correspondence should be addressed.

Molbank 2004, 2004(1), M353; https://doi.org/10.3390/M353

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

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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)δ(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)δ(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)

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

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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MDPI and ACS Style

Jarrahpour, A.A.; Zarei, M. Synthesis of a novel Schiff base {3,4-Bis[(2-Hydroxy-benzylidene) amino] phenyl} phenyl methanone. Molbank 2004, 2004, M353. https://doi.org/10.3390/M353

AMA Style

Jarrahpour AA, Zarei M. Synthesis of a novel Schiff base {3,4-Bis[(2-Hydroxy-benzylidene) amino] phenyl} phenyl methanone. Molbank. 2004; 2004(1):M353. https://doi.org/10.3390/M353

Chicago/Turabian Style

Jarrahpour, A. A., and M. Zarei. 2004. "Synthesis of a novel Schiff base {3,4-Bis[(2-Hydroxy-benzylidene) amino] phenyl} phenyl methanone" Molbank 2004, no. 1: M353. https://doi.org/10.3390/M353

APA Style

Jarrahpour, A. A., & Zarei, M. (2004). Synthesis of a novel Schiff base {3,4-Bis[(2-Hydroxy-benzylidene) amino] phenyl} phenyl methanone. Molbank, 2004(1), M353. https://doi.org/10.3390/M353

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

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