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To a cooled (0-5 C) solution of <strong>[40371-63-9]5-bromo-4-methyl-2-nitroaniline</strong> (0.400 g, 1.73 mmol) in DMF (20 mL) is added sodium hydride (0.077 g, 1.92 mmol). After 5 min., the ice bath is removed and the mixture is stirred at ambient temperature for 30 min. A solution of 1 - bromo-3-phenylpropane (0.290 mL, 1.90 mmol) in DMF (5 mL) is added and the mixture is stirred overnight at rt. Acetic acid (3 mL) is added and the mixture is concentrated. The residue is purified by flash chromatography (230-400 mesh, hexanes/ethyl acetate (0 to 1% containing 0.1% isopropanol) as eluant) to afford 0.540 g (89%) of the desired product as a yellow solid. NMR (CDC13) delta 2.08 (m, 2 H), 2.33 (s, 3 H), 2.80 (t, 2 H), 3.29 (q, 2 H), 7.03 (s, 1 H), 7.27 (m, 5 H), 7.91 (br t, 1 H), 8.03 (s, 1 H).
To a suspension of N-(5-bromo-4-methyl-2-nitrophenyl)acetamide (0.970 g, 3.55 mmol) in methanol (24.46 mL) is added 8.0 M aqueous HC1 (19.54 mL, 156.3 mmol). The mixture is heated at 70 C for 3 h, cooled, and the pH of the solution is adjusted to approximately 10 with solid NaHC03. The mixture is extracted with ethyl acetate and the combined organic extracts are washed with saturated, aqueous NaHC03, brine, dried (sodium sulfate), filtered and concentrated to afford 816 mg (99%) of the desired product as a yellow solid which is used without further purification. NMR (CDC13) delta 2.34 (s, 3 H), 5.9 (very broad exchangeable signal integrating for less than 2 H), 7.10 (s, 1 H), 7.99 (s, 1 H). MS (ESI+) for C7H7BrN202 m/z 233.1 (M+H)+.
With pyridine; for 19.0h;Inert atmosphere; Cooling with ice;
Stage 1 Stage 2 In a first step a solution of <strong>[40371-63-9]5-bromo-4-methyl-2-nitroaniline</strong> in dry pyridine under argon is cooled in an ice bath. 3-(chlorosulfonyl)benzoic acid is added and the reaction is stirred for 19 hours at room temperature. 1 ml water is added and the solvent is removed under reduced pressure. The yellow solid is taken up in water and 1M sodium hydroxide is added followed by EtOAc. After standing for a few minutes a yellow precipitate is formed. Intermediate is obtained as a white solid in 91% yield.
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