[CH3:1][O:2][C:3](=[O:12])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[N+:13]([O-])([OH:15])=[O:14].[OH-].[Na+].O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1100 ml of methylene chloride are introduced into a 2 l four-necked flask equipped with a stirrer, reflux condenser, thermometer and two dropping funnels, and 165.2 g (1 mol) of 4-tolylcarbamic acid methyl ester, dissolved in 500 ml of methylene chloride, and 102.9 g of 98% strength (1.6 mols) nitric acid dissolved in 200 ml of methylene chloride are added simultaneously in the course of 1 hour, at 10° C. and under normal pressure, the temperature being maintained by external cooling. After completion of the dropwise addition, the nitration mixture is allowed to come to 20° C. and is stirred for a further 1.75 hours, and the solution obtained is allowed to run, with stirring, into dilute sodium hydroxide solution, consisting of 480 ml of water and 144 g (3.6 mols) of NaOH, at 50° to 60° C., in the course of which methylene chloride distils off with a small amount of water. After the entire quantity of methylene chloride has distilled off, the temperature is raised to 95° C. and is maintained for 3 hours, whilst at the same time the methanol formed on hydrolysis of the 2-nitro-4-tolylcarbamic acid methyl ester to give the amino group is distilled off. The mixture is cooled to 60° C. and stirred for a further 30 minutes at 60° C., and the product is filtered off and washed alkali-free with water. The moist product is dried to constant weight in vacuo at 60° C. Yield: 145.4 g of dry product (94.9% of theory); purity: 99.3%.
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