M523 - 2-(Pyrazin-2-yliminomethyl)phenol

Molbank 2007, M523

http://www.mdpi.org/molbank/

2-(Pyrazin-2-yliminomethyl)phenol

Abdullah Mohamed Asiri *

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21413, P.O. Box 9028, Saudi Arabia

* Author to whom correspondence should be addressed. Tel: +966-2-6952293; Fax: +966-2-6952293; E-mail: [email protected]

Received: 5 April 2006 / Accepted: 27 September 2006 / Published: 31 May 2007

Keywords: Pyrazine, Anils, 2-hydroxy benzaldehyde, Schiff base

Schiff bases from 2-hydroxy-1-naphthaldehyde have often been used as chelating ligands in the field coordination chemistry [1]. The Schiff base compounds can be classified by their photochromic and thermochromic characteristics [2].

A solution of 2-aminopipyrazine 1 (5.0g, 0.052 mol) and 2-hydroxybenzaldehyde aldehyde 2 (6.97g, 0.052 mol) in absolute ethanol (100 mL) was heated under reflux for 3 hrs. Cooling the mixture, filtering the precipitate and recrystalization from ethanol gave the Schiff base 3 as yellow crystals (3.72g, 33.97%).

Melting Point: 96-98ºC (EtOH).

IR (KBr, cm^-1): 1594.9 (C=N), 1470 (C=C) and 1191.9 (C-N).

¹H NMR (400MHz; CDCl₃) δ, ppm: 12.67 (s, 1H, OH), 8.80 (s, 1H, CH _olefinic), 8.67 (d, 1H,, CH _aromatic), 8.51 (s, 1H,CH _aromatic), 8.50 (d, 1H, CH _aromatic), 7.69 (d, 1H, CH _aromatic), 7.27 (dd, 1H, CH _aromatic), 6.92 (d, 1H, CH _aromatic), 6.84 (dd, 1H, CH _aromatic).

Elemental Analysis: Calculated for C₁₁H₉N₃O(199.21): C, 66.32%; H 4.55%; N, 21.09 %. Found: C, 66.05%; H, 4.43 %; N, 21.14 %.

References:

1. Garnovski, A.D.; Nivorozhkin, A.L.; Minkin, V.I. Coord. Chem. Rev. 1993, 126, 1.

2. Hadjoudis, E.; Vittorakis, M.; Maustakali-Mavridis, I. Tetrahedron 1987, 43, 1345.