[C:1]([O:9]CC)(=[O:8])[CH2:2][C:3](OCC)=O.[N+:12]([C:15]1[CH:22]=[CH:21][C:18](CBr)=[CH:17][CH:16]=1)([O-:14])=[O:13].[H-].[Na+].[OH-].[Na+]>C1COCC1.O.C(O)C>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:3][CH2:2][C:1]([OH:9])=[O:8])=[CH:17][CH:16]=1)([O-:14])=[O:13]
Alkylation of diethyl malonate with 4-nitrobenzyl bromide using sodium hydride in THF, followed by ester hydrolysis with sodium hydroxide in water and ethanol, then heating the resulting diacid to its melting point causing decarboxylation gives 3-(4-nitro-phenyl)-propionic acid. Conversion to the acid chloride with thionyl chloride in DCM and coupling with 2-amino-4,6-dimethylpyridine affords N-(4,6-dimethyl-pyridin-2-yl)-3-(4-nitro-phenyl)-propionamide. Amide reduction with borane-dimethylsulfide in THF at reflux, methylation of the resulting amine with methyl iodide and sodium hydride in THF and finally catalytic hydrogenation over Raney nickel in methanol gives the required aniline.
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