Two thermochromic Schiff bases mostly in keto-amine tautomeric form were obtained by means of mechanochemical synthesis. Both Schiff bases Compound 1 and Compound 2, respectively are derived from the same primary amine 2-amino-5-methylphenol. Salicylaldehyde was used as aldehyde component in preparation of 1, and o-vanillin as substituted salicylaldehyde component in synthesis of 2. Powder products of the neat grinding and liquid-assisted grinding syntheses of 1 and 2 were compared with the crystalline products, obtained by recrystallization from a small amount of solvent. Both raw powder and recrystallized products were characterized and compared by means of PXRD, DSC and IR.