2,6-Dichloroaniline → HCID 86639846, compound

Participants

Reaction Steps

To a solution of (2,6-dichlorophenyl)amine (12.8 g) in THF (73 mL) was added an 1 M THF solution of lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (79.8 mL) at 0° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 30 min. To this solution was added a solution of dimethyl (2E,4Z)-4-(methoxymethylene)-2-pentenedioate (14.52 g) in THF (35 ml) at once, and the resulting mixture was stirred at 0° C. for 3 hr. The reaction mixture was diluted with EtOAc (150 mL) and washed with a mixture of 1 M HCl (200 mL) and brine (150 mL), saturated aqueous NaHCO3 (150 mL) and brine successively, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with a mixture of EtOAc and hexane (1:2) and collected by filtration to give dimethyl (2E,4Z)-4-{[(2,6-dichlorophenyl)amino]methylene}-2-pentenedioate (9.28 g). The filtrate was evaporated in vacuo and the residue was purified by silica gel (200 g) column chromatography eluting with EtOAc-hexane (1:2) followed by triturating the isolated material with EtOAc-hexane (1:2) to afford dimethyl (2E,4Z)-4-{[(2,6-dichlorophenyl)amino]methylene}-2-pentenedioate (1.30 g).

Provenance & Evidence