Ethyl Acetate → 2-Chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine

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Reaction Steps

To 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine (3.6 g, 10 mmol) in THF (50 mL) and water (50 mL) was added sodium hydrosulfite (10.2 g, 50 mmol). The mixture was stirred at ambient temperature for 2 hrs. Ethyl acetate (150 mL) and sat. NH4Cl (150 mL) were added. The organic layer was separated, washed with brine (2×50 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (4/1 to 1/1) yielded 2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine as pale yellow solid (3.4 g). MS: 337.0 (M+H)+; tR=2.85 min (method 1).

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