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Evolution of gas with alkaline pH and characteristic amine odor was detected
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Evolution of gas with alkaline pH and characteristic amine odor was detected.
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54
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62349096771
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All melting points were determined on a Büchi apparatus and are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker AM 300 spectrometer in CDCl3 with TMS as internal standard. All coupling constants are given in Hz and chemical shifts are given in ppm. Typical Experimental Procedure for the Preparation of 3e: To a stirred solution of o-phenylenediamine (1a; 1.0 mmol) in toluene (20 mL, 4-chlorobenzaldehyde (1.0 mmol) was added and stirring was continued for 5 min. Then TosMIC (1.0 mmol) and DABCO (1.2 mmol) were added and the reaction mixture was heated to 80°C for 4 h. The resulting solution was initially washed with 5% HCl, then with H2O and dried. The solvent was distilled off under reduced pressure to yield the corresponding crude product mixture, which was purified by silica gel chromatography using petroleum ether-EtOAc (10:1) as eluent, to give quinoxaline 3e in 84% yield; yellow
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2 (240.69): C, 69.85; H, 3.74; N, 11.64. Found: C, 70.01; H, 3.83; N, 11.68.
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62349098314
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The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from
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The multiplicities and chemical shifts of the aromatic protons have been confirmed after simulation with program SpinWorks, version 2.5, available from ftp://davinci.chem.umanitoba.ca.
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