S(Cl)(Cl)=O.CN(C)C=O.O[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].C(N(CC)CC)C.[CH2:31]([CH2:33][NH2:34])[OH:32]>ClCCl>[N+:21]([C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[NH:34][CH2:33][CH2:31][OH:32])=[CH:19][CH:18]=[CH:17][CH:16]=2)([O-:23])=[O:22]Thionyl chloride (32.3 mL, 0.4338 mole) and N,N-dimethylformamide (32 mL, 0.4338 mole) were added sequentially to a suspension of 4-hydroxy-3-nitroquinoline (75 g, 0.3944 mole) in dichloromethane (750 ml). The reaction mixture was heated at reflux for about 2½ hours and then held at ambient temperature overnight. The reaction mixture was chilled in an ice bath and then a mixture of triethylamine (82.5 mL, 0.5916 moles) and ethanolamine (35.7 mL, 0.5916 mole) in dichloromethane was slowly added. The reaction mixture was heated at reflux for several hours and then an additional 0.5 equivalents of both triethylamine and ethanolamine were added. The reaction mixture was refluxed for an additional hour then held at ambient temperature overnight. The resulting solid was isolated by filtration, washed first with dichloromethane then with water, and dried to provide 75 g of 2-[(3-nitro-4-quinolinyl)amino]ethanol.
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