Hydrochloric Acid → HCID 22268744, compound

Participants

Reaction Steps

Methyl 3-(trifluoromethylcarbonyl)amino-5-(trifluoromethyl)benzoate (cf. procedures (116a) and (80a); 131 mg, 0.42 mmol) was dissolved in THF (5 mL), and the resultant solution was charged successively with KHMDS (0.83 mL of a 0.5 M solution) and iodomethane (0.03 mL, 0.42 mL). The mixture was stirred for 16 h, quenched with sat. NaHCO3, and extracted with EtOAc (2×). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. This product was dissolved in 3:1:1 THF/MeOH/water (5 mL) and the resultant solution was charged with lithium hydroxide (20 mg, 0.84 mmol). The reaction was stirred for 14 h, acidified with 1N HCl, and extracted with EtOAc (2×). The organic extracts were combined, washed with water, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide 3-methylamino-5-(trifluoromethyl)benzoic acid.

Provenance & Evidence