4-methylquinoline

Description

Refer to 6-METHYLQUINOLINE.

Chemical properties

clear slightly yellow to brown liquid

Physical properties

4-Methylquinoline is a colorless liquid with a weak quinoline-like odor. It is slightly soluble in water, miscible with many organic solvents, and volatile in steam.

The Uses of 4-methylquinoline

Lepidine is used in the preparation of certain dyes.

The Uses of 4-methylquinoline

4-Methylquinoline is used as a reagent in the synthesis of azetidine based ene-amides as potent bacterial enoyl ACP reductase inhibitors. Also used as a reagent in the synthesis of cyanine-styryl dyes with enhanced photostability for fluorescent DNA imaging.

Definition

ChEBI: A methylquinoline carrying a methyl substituent at position 4.

Production Methods

4-Methylquinoline can be recovered from the highest-boiling fraction of the coal-tar quinoline bases via its o-cresol addition compound. It can be synthesized by condensation of aniline and methyl vinyl ketone.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

General Description

Synthesis of lepidine from 4-anilinobutan-2-one in ethanol in the presence of HCl or FeCl₃ has been reported. Nitration of lepidine has been reported.

Purification Methods

Reflux lepidine with BaO, then fractionally distil it. Further purify it via its recrystallised dichromate salt (m 138o) (from H2O). [Cumper et al. J Chem Soc 1176 1962.] [Beilstein 20 III/IV 3477, 20/7 V 389.]