Substituted Amides of 4-Nitro-2,2'-diphenic Acid
Abstract Generated abstract
This study reports the synthesis of nine previously undescribed substituted monoamides of 4-nitro-2,2'-diphenic acid as part of a search for biologically active derivatives related to earlier 2,2'-diphenic acid amides. The compounds were prepared by reacting 4-nitro-2,2'-diphenic anhydride with various amines in dry xylene, followed by isolation, acid precipitation from sodium carbonate solution, and recrystallization. The products were characterized as crystalline, water-insoluble substances whose alkali-metal salts are readily water soluble, with melting points, crystal appearance, empirical formulas, and nitrogen analyses reported. Testing of the sodium salts as intestinal poisons for flies showed low insecticidal activity, suggesting that introduction of a nitro group reduced activity relative to analogous 2,2'-diphenic acid amides.
Full Text
SUBSTITUTED AMIDES OF 4-NITRO-2,2′-DIPHENIC ACID
L. P. Kulev, G. M. Stepnova, P. F. Tabinskaya
Earlier [1, 2] we obtained substituted monoamides of 2,2′-diphenic acid. Some of them exhibited high herbicidal and insecticidal activity. In order to search for new biologically active compounds, several substituted monoamides of 4-nitro-2,2′-diphenic acid were synthesized. The compounds described are crystalline substances, insoluble in water but soluble in common organic solvents. Monoamides with alkali metals give salts readily soluble in water. The sodium salts of substituted monoamides of 4-nitro-2,2′-diphenic acid were tested on flies as intestinal poisons. In contrast to sodium salts analogous to the amides of 2,2′-diphenic acid, they showed low insecticidal activity, i.e., in this case the introduction of a nitro group caused a decrease in biological activity.
Experimental Part
0.05 mole of amine, 0.05 mole of nitrodiphenic anhydride (obtained from 4-nitro-2,2′-diphenic acid by heating with acetic anhydride), and 50 ml of dry xylene are placed in a flask fitted with a reflux condenser and a stirrer. The flask is heated on an oil bath at a temperature
Table 1
| Acylated amine | Empirical formula | m.p., °C | Crystal color | Nitrogen, % found | Nitrogen, % calculated |
|---|---|---|---|---|---|
| Methylamine | C₁₅H₁₂O₅N₂ | 220 | light yellow | 9.40 | 9.33 |
| Dimethylamine | C₁₆H₁₄O₅N₂ | 204 | ″ ″ | 9.20 | 8.92 |
| 2-Toluidine | C₂₁H₁₆O₅N₂ | 206 | colorless | 7.42 | 7.45 |
| 3-Toluidine | C₂₁H₁₆O₅N₂ | 211 | ″ | 7.68 | 7.45 |
| 4-Toluidine | C₂₁H₁₆O₅N₂ | 238 | ″ | 7.60 | 7.45 |
| 2-Nitroaniline | C₂₀H₁₃O₇N₃ | 232 | ″ | 10.20 | 10.32 |
| 3-Nitroaniline | C₂₀H₁₃O₇N₃ | 248 | light yellow | 10.26 | 10.32 |
| 4-Nitroaniline | C₂₀H₁₃O₇N₃ | 221 | ″ ″ | 10.41 | 10.32 |
| 4-Chloroaniline | C₂₀H₁₃O₅N₂Cl | 230 | colorless | 7.63 | 7.58 |
135–140°C for 3 hours. The precipitate that separates after cooling the reaction mixture is filtered off, dried, dissolved in a 10% sodium carbonate solution, and the monoamide is precipitated with acid. Recrystallization is carried out from alcohol, xylene, or chlorobenzene.
The characteristics of the compounds obtained are given in Table 1.
Conclusions
Nine substituted monoamides of 4-nitro-2,2′-diphenic acid, not previously described in the literature, have been synthesized. Their insecticidal activity has been determined.
References
- L. P. Kulev, G. M. Stepnova. Izv. TPI, vol. 111, 16, 1961.
- L. P. Kulev, G. M. Stepnova. Izv. TPI, vol. 111, 20, 1961.