C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:7]([N+:17]([O-:19])=[O:18])[CH:6]=1)C.C1COCC1.[OH-].[Na+].Cl>C(O)C>[CH2:13]([CH:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[CH:6][C:7]=1[N+:17]([O-:19])=[O:18])[CH2:15][CH3:16])[CH3:14]30.0 g of 4-(1-ethyl-propylamino)-3-nitro-benzoic acid ethyl ester were dissolved in 100 ml ethanol and 10 ml THF and 107 ml of 2 M aqueous sodium hydroxide solution were added. After stirring at room temperature over night, the reaction mixture was brought to pH 1 by addition of 2 M aqueous hydrochloric acid and extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulphate and concentrated to yield 27.0 g (100%) of 4-(1-ethyl-propylamino)-3-nitro-benzoic acid as a yellow solid.
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