[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[Cl:16][Sn]Cl>O.Cl.CC(O)=O>[ClH:16].[NH:5]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10])[NH2:1]A solution of 2.74 g of NaNO2 in 28 ml of water is added over 30 minutes to a solution, cooled to -5° C., of 5 g of 3-amino-4-methylbenzoic acid in 120 ml of concentrated HCl and 40 ml AcOH, and the mixture is left stirring for 1 hour 20 minutes at 0° C. After cooling to -10° C., a solution of 27.6 g of SnCl2 ·2H2O in 28 ml of concentrated HCl is added slowly. After stirring for 1 hour at RT, filtration, washing of the precipitate with 5 ml of 1N HCl and drying over P2O5 under vacuum, 6.15 g of the expected product are obtained.
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