2,2-DIALKYL-NAPHTHIMIDAZOLINE QUINONES .5. HETEROCYCLIC 1,4-NAPHTHOQUINONE DERIVATIVES (1)

In ethanolic hydrochloric acid 2-monochloro-/2-dichloroacetylamino-3-(2-methylanilino)-1,4-naphthoquinone 7/8 cyclisize to give 2-2-monochloromethyl-/2-dichloromethyl-naphthimidazoline quinones 12/13. The hydrolysis of 7/8 yields 2-amino-3-(2-methylanilino)-1,4-naphthoquinone (11a). The condensation from 11a with acetone, included in ethanol as impurity, give the blue 2,3,4,9-tetrahydro-2,2-dimethyl-1-(2-methylphenyl)-1H-naphtho[2,3-d]imidazole-4,9-dione (15a), the third reaction product. By condensation from 11a with other ketones the naphthimidazole quinones 15b-h are obtained. This color reaction from 11a can be used to detect such ketones.