Quinaldine (2-methylquinoline) is an organic compound derived from quinoline with the chemical formula C 10 H 9 N. Used for the synthesis of dyes, drugs and other organic compounds. It is an isomer of lepidine .
| Hinaldin | |
|---|---|
| Are common | |
| Chem. formula | C₁₀H₉N |
| Physical properties | |
| Density | 1.0585 g / cm³ |
| Thermal properties | |
| T. melt. | -1 ° C |
| T. bale. | 247.6 ° C |
| Optical properties | |
| Refractive index | 1.6126 |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Content
History
The synthesis was first carried out by Döbner and Miller in 1881 by the Skraup reaction from ethylene glycol. Subsequently, they obtained it from aniline with paraldehyde and sulfuric acid [1] .
Physical and chemical properties
A colorless liquid with a melting point of −1 ° C, a boiling point of 247.6 ° C, a density of 1.0585 g / cm 3 and a refractive index of 1.6126. Slightly soluble in water, soluble in organic solvents [2] .
Forms salts with inorganic acids and alkylating agents. Condensed with aldehydes . The hydrogen atom in the methyl group is mobile, as a result of which the substance can form organometallic compounds. Enters into the Mannich reaction [2] .
Selenium dioxide oxidizes the methyl group to the aldehyde. Chromic acid - up to carboxylic acid [2] .
When interacting with permanganates, it forms anthranilic acid [2] .
Getting
Usually obtained from the quinoline fraction of coal tar [2] .
It can be synthesized according to the Döbner-Miller method. For this, the Scraup reaction is carried out in which glycerin is replaced by ethylene glycol. Another modification of the same method is the production of quinaldine from aniline, paraldehyde and sulfuric acid. Replacing sulfuric acid with hydrochloric acid and adding a small amount of zinc chloride increases the yield of the reaction [3] [4] .
Application
Used for the synthesis of quinaldic acid, dyes, drugs [2] .
Notes
- ↑ Elderfield, 1955 , p. 9.
- ↑ 1 2 3 4 5 6 Knunyants, 1983 .
- ↑ Elderfield, 1955 , p. 9-10.
- ↑ Mikeska, 1919 , p. 457.
Literature
- Khinaldin: article // Chemical Encyclopedic Dictionary / Ch. ed. Knunyants I.L. - M .: Soviet Encyclopedia , 1983. - S. 654. - 792 p.
- Elderfield R. Heterocyclic Compounds / Ed. Elderfield R. - M .: Publishing House of Foreign Literature, 1955. - T. 4.
- Mikeska LA, Stewart JK, Wise LE Intermediates Used in the Preparation of Photosensitizing Dyes. I — Quinoline Bases (Eng.) // The journal of industrial and engineering chemistry: Journal. - 1919. - Issue. 11 . - No. 5 . - S. 456–458 . - DOI : 10.1021 / ie50113a024 .