Synthesis of certain 1 and 3-substituted indolin-2-ones

2-Bromo-4-methyl-phenylthiosemicarbazide (IV) prepared from 2-bromo-4-methylaniline hydrochloride (11), was condensed with 5-methyl isatin and 5-methyl-7-bromo isatin to form the corresponding condensation product 5-methyl-3-(2-bromo-4-methyphenylthiosemicarbazono)-2-indolinone (Va) and 5-methyl-7-bromo-3-(2-bromo-4-methylphenyl thiosemicarbazono)-2-indolinone Vb respectively while 2-bromo-4-methyl aniline hydrochloride was condensed with 5-methyl/5-methyl-7-bromoisatin to form 5-methyl/5-methyl-7-bromo-3-(2-bromo-4-methyl-phenylimino)-2-indolinones (IXa,b). Mannich condensation of V with HCHO and amines yielded VI-VIII. Characterization of new compounds has been done by mean of IR and H-1 NMR spectral data and elemental analysis.