2-Chloro-4-nitrobenzoic acid → HCID 10853940, compound

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Reaction Steps

A solution of 42.6 g (0.211 mol) of 2-chloro-4-nitrobenzoic acid is reacted with 420 ml of thionyl chloride (refluxed for 3 hours and the excess thionyl chloride removed). Toluene is added several times and the solvent removed. The residue is dissolved in 400 ml of CH2Cl2 and added dropwise to a cold (ice bath) solution of 28.2 g (0.192 mol) of 1,2,3,4-tetra-hydro-5H-1-benzazepine and 29.4 ml of triethylamine in 320 ml of dichloromethane. The mixture is stirred at room temperature overnight and is washed with H2O, 10% HCl and 10% NaHCO3. Activated carbon is added to the organic layer and the mixture is filtered through a layer of MgSO4. The solvent is removed under vacuum and the residue chromatographed on silica gel (in two batches) with ethyl acetate-CH2Cl2 (5:95) as eluent. The fractions containing product are combined and the solvent removed. The residue is dissolved in ethyl acetate and the solvent removed (foams). The residue is heated with hexane to give a solid (lumps broken up) and the mixture is filtered. The solid is washed with hexane and dried to give 59.9 g of 1,2,3,4-tetrahydro-1-(2-chloro-4-nitrobenzoyl)-5H-l-benzazepine as off-white crystals, m.p. 112°-114° C., mass spectrum (CI) 321 (MH+)

Provenance & Evidence