4-Nitrobenzaldehyde → 2-amino-1-(4-nitrophenyl)ethanol

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Reaction Steps

The method of Schoenenberger, Archiv. der Pharmazie, 1975, 308(9), 717-719 can be employed. 4-Nitrobenzaldehyde can be reacted with nitromethane and base, followed by selective reduction of the aliphatic nitro group to yield 1-amino-2-hydroxy-2-(4-nitrophenyl) ethane. This substance can be reacted with 2,6-dichlorobenzaldehyde to yield a mixture of cis-(±) and trans-(±)-2-(2,6-dichlorophenyl)-5-(4-nitrophenyl)-1,3-oxazolidines. The nitrophenyl group can be reduced with tin (II) dichloride or iron powder and ammonium chloride to yield the corresponding aniline. This aniline can be reacted with 2,2-dichloroacetyl chloride and triethylamine to yield a mixture of cis-(±) and trans-(±)-2,2-dichloro-N-[4-[2-(2,6-dichlorophenyl)-5-(1,3-oxazolidinyl)]phenyl]acetamides.

Provenance & Evidence