[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)[CH3:2].[S:14](=[O:18])(=[O:17])([OH:16])[OH:15].[N:19](OC(C)C)=O.[H][H]>[C].[Pd].C(O)(C)C>[S:14]([OH:18])([OH:17])(=[O:16])=[O:15].[NH2:19][C:7]1[CH:8]=[CH:9][C:4]([N:3]([CH2:1][CH3:2])[CH2:11][CH2:12][OH:13])=[CH:5][C:6]=1[CH3:10]
With 89.6 g (0.5 mole) of N-ethyl-N-(β-hydroxyethyl)-m-toluidine was mixed 270 ml of 50% v/v isopropanol, and 24.5 g (0.25 mole) of sulfuric acid was added with cooling and stirring at 10° C. or lower. After 49.0 g (0.55 mole) of isopropyl nitrite was added dropwise at 10° C. or lower, the reaction was carried out at 2°-5° C. for another 3 hours. After completion of the reaction, hydrogenation was carried out at 40°-45° C. and at a hydrogen pressure of 3-5 kg/cm2 while adding the nitrosation reaction mixture to 270 ml of 50% v/v isopropanol containing 6.5 g of 5% palladium-carbon over a period of 2 hours. After completion of the hydrogenation, the catalyst was filtered off and the filtrate was concentrated to dryness to remove the solvent. The residue was dissolved in 270 ml of 90% v/v ethanol with heating and 24.5 g (0.25 mole) of sulfuric acid was added at 45°-50° C. Then, the resulting mixture was cooled for 2 hours to carry out crystallization, and the crystals thus formed were collected by filtration at 3° C., washed with 100 ml of cold ethanol, and then dried to obtain 133.3 g of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate as white powder. Yield: 91.2%. Melting point: 154.6° C. The purity of 4-amino-3-methyl-N-ethyl-N-(β-hydroxyethyl)aniline sulfate was 100% as measured by HPLC, namely, no impurity was detected at all.
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