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Concentrated HCl (15 mL) was slowly added dropwise to a mixture of nitroaniline 8, 13c-d (12 mmol), and tin (30 mmol). The reactionmixture was heated at reflux for 1.5 h, cooled to r.t., and neutralizedwith 50% NaOH solution to pH 9-10. The precipitate was filtered off,dried, and extracted with hot EtOAc (80 mL). Diamines 10 and 14c-dwere obtained after evaporation of filtrates.3,4,5-Trifluoro-1,2-phenylenediamine (10)Yield: 1.40 g (70%); brown crystals; mp 85-87 C; Rf 0.72
With KNO3; sulfuric acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethyl acetate;
3,4,5-Trifluoro-1,2-phenylenediamine. To 2,3,4-trifluoroacetanilide (1.35 g, 7.09 mmol) is added concentrated sulfuric acid (8 mL). While the flask is in an ice bath, KNO3 is slowly added, giving a tan mixture, that is stirred overnight. The reaction mixture, now dark red, is then added to ice water (45 mL), instantly giving an orange precipitate. The volatile compound, presumably 2,3,4-trifluoro-6-nitroaniline, is dissolved in ethyl acetate (18 mL) and ethyl alcohol (12 mL). To the orange solution is added stannous chloride dihydrate (7.6 g, 34 mmol). The resulting mixture is stirred and brought to reflux under N2 for 4 h. The mixture is added to ice water (40 mL) and basified with 2N NaOH (40 mL). It is extracted with ethyl acetate (3*20 mL) and the combined extracts are washed with water (20 mL) and brine (20 mL). This dark red solution is dried (MgSO4) and evaporated to give 285 mg (25%) of the diamine as a dark red solid. 1 H NMR (CDCl3), 3.22 (br s, 2H), 3.46 (br s, 2H), 6.32 (m, 1H).
285 mg (25%)
With KNO3; sulfuric acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethyl acetate;
3,4,5-Trifluoro-1,2-phenylenediamine To 2,3,4-trifluoroacetanilide (1.35 g, 7.09 mmol) is added concentrated sulfuric acid (8 mL). While the flask is in an ice bath, KNO3 was slowly added, giving a tan mixture, which was stirred overnight. The reaction mixture, now dark red, was then added into ice water (45 mL), instantly giving an orange precipitate. The volatile compound, presumably 2,3,4-trifluoro-6-nitroaniline, is dissolved in ethyl acetate (18 mL) and ethyl alcohol (12 mL). To the orange solution is added stannous chloride dihydrate (7.6 g, 34 mmol). The resulting mixture is stirred and brought to reflux under N2 for 4 h. The mixture is added into ice water (40 mL) and basified with 2N NaOH (40 mL). It was extracted with ethyl acetate (3*20 mL) and the combined extracts were washed with water (20 mL) and brine (20 mL). This dark red solution is dried (MgSO4) and evaporated to give 285 mg (25%) of the diamine as a dark red solid. 1 H NMR (CDCl3), 3.22 (br s, 2H), 3.46 (br s, 2H), 6.32 (m, 1H).
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