Oxygen → 2-Iodo-4-methylaniline
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[I-:1].[NH4+].P([O-])(O)(O)=O.[NH4+].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.O=O>[Cu](I)I.O.C1C=CC=CC=1>[I:1][C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[NH2:9][I-:1].[NH4+].P([O-])(O)(O)=O.[NH4+].[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.O=O>[Cu](I)I.O.C1C=CC=CC=1>[I:1][C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[NH2:9]To a 500-ml pressure-proof glass autoclave were added 150 g (1.03 mole) of ammonium iodide, 5 g (0.0262 mole) of copper iodide, 50 g (0.435 mole) of ammonium dihydrogenphosphate, 70 g (0.654 mole) of p-toluidine, 250 ml of benzene and 100 ml of pure water, and reaction was carried out with stirring under a condition that the oxygen pressure be 3 to 8 kg/cm2 (gauge pressure) and the temperature be 70° C. At the point when the oxygen pressure decreased from 8 kg/cm2 to 3 kg/cm2, oxygen was supplied again to 8 kg/cm2. After 3 hours, the organic layer was taken out, and 83.1 g (0.357 mole) of 2-iodo-4-methylaniline was obtained from this layer. The yield was 82%.
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