C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH2:16][CH3:17])[CH:10]=1.CC([O-])=O.[K+].[N:23](OCCC(C)C)=O.C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)Cl>[C:5]([N:13]1[C:12]2[C:11](=[CH:10][C:9]([Br:8])=[CH:15][CH:14]=2)[C:16]([CH3:17])=[N:23]1)(=[O:7])[CH3:6]Acetic anhydride (4.73 ml) was added to the mixture of 4-bromo-2-ethylaniline (5.0 g) and KOAc (2.94 g) in CHCl3 (70 ml) and stirred for 30 minutes at reflux. Then isoamyl nitrite (6.65 ml) and 18-crown-6-ether (660 mg) was added to the reaction mixture and stirred for 12 h. under reflux. The reaction mixture was diluted with CHCl3, washed with water, and dried over sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (hexane/EtOAc), and crystallized from mixed solvent of hexane and CHCl3 to give intended compound as a yellow solid.
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