[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16].[Cl:17][Sn]Cl>O.Cl>[ClH:17].[NH:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[O:15][CH3:16])[NH2:1]A solution of 2.17 g of NaNO2 in 40 ml of H2O is added slowly to a solution, cooled to 0° C., of 5 g of 4-amino-3-methoxybenzoic acid in 50 ml of concentrated HCl. After 1 hour 15 minutes of stirring at 0° C., the mixture is cooled to -10° C., and a solution of 23.6 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 min. After one and a half hours of stirring at -10° C., the mixture is filtered, and the precipitate is washed with 50 ml of pentane to obtain, after drying, 6 g of expected product.
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