Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:30][C:24]([CH3:31])([CH2:23][NH:22][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[C:25]([O:27][CH2:28][CH3:29])=[O:26]
A suspension of 4-chloro-3-nitroquinoline (35.0 g, 168 mmol) and triethylamine (84 mL, 0.60 mol) in dichloromethane (400 mL) was cooled to 0° C.; a solution of ethyl 3-amino-2,2-dimethylpropanoate (40.0 g, 0.220 mol) in dichloromethane (50 mL) was added dropwise. The reaction was stirred at 0° C. for 30 minutes and then at ambient temperature for four hours. The reaction was incomplete as determined by a TLC analysis, and additional ethyl 3-amino-2,2-dimethylpropionate (10.0 g, 55.0 mmol) was added. The reaction was stirred overnight; another analysis by TLC indicated the reaction was incomplete. Additional ethyl 3-amino-2,2-dimethylpropionate (5.0 g, 28 mmol) was added, and the reaction was heated at reflux for three hours. Potassium carbonate (10 g) was added, and the reaction was heated at reflux for two hours and stirred overnight at ambient temperature. Saturated aqueous sodium bicarbonate (50 mL) was added, and the reaction was stirred for three days. The organic layer was separated, washed with water (3×100 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide ethyl 2,2-dimethyl-3-[(3-nitroquinolin-4-yl)amino]propanoate as an orange oil, which was mixed with material from another run and used without purification.
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