Triethylamine → 4-Dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide

Participants

Reaction Steps

4-dimethylamino-6-[3-(trifluoromethyl)phenoxy] picolinic acid (0.64 g, 0.0020 mol) was mixed with thionyl chloride (0.50 g, 0.0020×2.1 mol) and benzene (about 10 ml), and further with a small amount of dimethyl formamide. Thereafter, the resultant mixture was refluxed for about 30 minutes. The obtained reaction solution was concentrated and then dissolved in dichloromethane (about 30 ml). The obtained solution was mixed with N,N-dibenzyl hydrazine (0.66 g, 0.0020×1.6 mol) and further with triethyl amine (0.53 g, 0.0020×2.6 mol). After the resultant mixture was stirred at room temperature for about one hour, the obtained reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and the organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated. The obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Provenance & Evidence