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The N-(3, 5-Dichlorophenyl) naphthaldimine was obtained from the reaction of 2-hy- droxynaphthalene-l-carbaldehyde (0.01 mol) with a solution of 2-bromo-4-methylaniline (0.01 mol) in 40 ml of ethanol. Reaction of 2-bromo-4-methylaniline was quite clean, albeit 3,4-diaminotoluene was isolated just in 37% yield after flash chromatography on silica gel. The bromomethylquinoline starting material 16 was synthesized in two steps using an optimized process route by condensing 2-bromo-4-methylaniline.
Renee Aspiotis,; Denis Deschênes,; Daniel Dubé,; Yves Girard,; Zheng Huang,; France Laliberté,; Susana Liu,; Robert Papp,; Donald W. Nicholson,; Robert N. Young.The discovery and synthesis of highly potent subtype selective phosphodiesterase 4D inhibitors. Bioorganic & Medicinal Chemistry Letters 2010, 20(18), 5502-5505.
A. Elmali,; Y. Elerman,; I. Svoboda and H. Fuess. N-(3,5-Dichlorophenyl)naphthaldimine. Acta Cryst.. 1998, c54 974-976.
Hazard Statements: H301-H311-H315-H319
Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P280h-P305+P351+P338-P309-P310a-P302+P352a
Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor IF ON SKIN: Wash with plenty of water.