The reaction of 2,6-dichloro-3-nitrotoluene (I) with CuCN in hot DMF gives the benzonitrile (II), which is brominated with 1,3-dibromo-5,5-dimethylhidantoin (DBDH) and benzoyl peroxide in hot chlorobenzene yielding the benzyl bromide (III). The reaction of (III) with 2-methyl-8-quinolinol (IV) by means of K2CO3 or Cs2CO3 in DMF affords the benzyl ether (V), which is reduced at the nitro group with SnCl2 giving the amino derivative (VI). The condensation of (VI) with 2-phthalimidoacetyl chloride (VII) by means of DMAP and pyridine in refluxing dichloromethane yields the corresponding amide (VIII), which is N-methylated with methyl iodide and NaH in DMF affording intermediate (IX). Elimination of the phthalimido group of (IX) with hydrazine in refluxing dichloromethane/methanol provides the substituted glycinamide (X), which is finally acylated with 3-(3-methoxyphenyl)-2(E)-propenoyl chloride (XI) by means of triethylamine in refluxing dichloromethane.

The reaction of 2,6-dichloro-3-nitrotoluene (I) with CuCN in hot DMF gives the benzonitrile (II), which is brominated with 1,3-dibromo-5,5-dimethylhidantoin (DBDH) and benzoyl peroxide in hot chlorobenzene yielding the benzyl bromide (III). The reaction of (III) with 2-methyl-8-quinolinol (IV) by means of K2CO3 or Cs2CO3 in DMF affords the benzyl ether (V), which is reduced at the nitro group with SnCl2 giving the amino derivative (VI). The condensation of (VI) with 2-phthalimidoacetyl chloride (VII) by means of DMAP and pyridine in refluxing dichloromethane yields the corresponding amide (VIII), which is N-methylated with methyl iodide and NaH in DMF affording intermediate (IX). Elimination of the phthalimido group of (IX) with hydrazine in refluxing dichloromethane/methanol provides the substituted glycinamide (X), which is finally acylated with 3-(3-methoxyphenyl)-2(E)-propenoyl chloride (XI) by means of triethylamine in refluxing dichloromethane.