[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(=O)(=O)(O)O.[N:19](OC(C)C)=[O:20]>C(O)(C)C>[CH2:1]([N:3]([CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][C:7]([N:19]=[O:20])=[C:6]([CH3:10])[CH:5]=1)[CH3:2]With 89.6 g (0.5 mole) of N-ethyl-N-(β-hydroxyethyl)-m-toluidine was mixed 270 ml of 80% 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° C. or lower for another 4 hours. After completion of the reaction, the crystals precipitated were collected by filtration to obtain 119.7 g of N-ethyl-N-(β-hydroxyethyl)-3-methyl-4-nitrosoaniline.1/2 sulfate as yellow-green powder. Yield: 93.0%. Decomposition point: 74° C.
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