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.
Uses
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.
Uses
4-methylquinoline is used mainly in flavor compositions for imitation Honey, Nut, Butter,
Caramel, etc. and in certain fruit complexes.
The concentration used is normally about 0.2
to 2 ppm in the finished product.
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.
General Description
Synthesis of lepidine from 4-anilinobutan-2-one in ethanol in the presence of HCl or FeCl
3 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.]
