[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:12])[C:8]=1[O:9][CH2:10][CH3:11])[NH2:5].[N:13]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[Na+]>Cl.O.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][NH2:13])[CH:6]=[C:7]([CH3:12])[C:8]=1[O:9][CH2:10][CH3:11]
To a cooled (+5° C.), stirred suspension of 9.2 g (0.0557 mol) of 3,5-dimethyl-4-ethoxyaniline in 50 ml of 6N HCl (aq), 3.8 g (0.0557 mol) of NaNO2 in 15 ml of water was added during 30 minutes. After stirring at +5° C. for 30 minutes further, the resulting mixture was added under argon and stirring to 29.1 g (0.167 mol) of sodium dithionite dissolved in 150 ml of water. After stirring for 20 minutes at +5° C., 250 ml of ether was added followed by alkalinization to pH 9 with 10N sodium hydroxide solution. The organic phase was separated and washed with sodium chloride solution. After drying (Na2SO4) the product was precipitated as the hydrochloride by addition of HCl(g)/ether (to pH 3). Filtration and washing with ether gave 9.4 g (78%) of the product.
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