Hydrochloric Acid → HCID 67056852, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-4-chlorobenzoic acid (3.99 g) in THF (35 mL) was added dropwise an 1 M THF solution of lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (46.5 mL) while keeping the internal temperature below −5° C. under a nitrogen atmosphere, and the mixture was stirred for 15 min around −10° C. Powder of methyl 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (3.46 g) was added to the mixture at once, and the resulted mixture was stirred at the same temperature for 3 hr under a nitrogen atmosphere. The reaction mixture was poured into a mixture of ice-water (700 mL) and 1 M HCl (100 mL), and the resulting mixture was extracted with EtOAc (150 mL×3). During the extraction, undissolved materials were produced, which were removed by filtration. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The filtrate was evaporated in vacuo, and the residue was triturated with MeOH, and the precipitates produced were collected by filtration to give 4-chloro-3-({[1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]carbonyl}amino)benzoic acid (1.74 g).

Provenance & Evidence