Sodium Hydroxide → 4-(2-((4-Methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Prepared using General Procedure 9: To a stirring solution of methyl 4-(2-((4-methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoate INT-54 (113 mg, 0.31 mmol) in EtOH (10 mL) was added 1 N NaOH (1 mL). The reaction mixture was heated to 50° C. for 3 h, concentrated, diluted with water, acidified with 1 N HCl and extracted with EA and DCM. The organic layers were combined, dried over Na2SO4 and concentrated to provide 97 mg (89%) of 4-(2-((4-methoxy-2-(trifluoromethyl)phenyl)amino)-2-oxoethyl)benzoic acid INT-55. LCMS-ESI (m/z) calculated for C17H14F3NO4: 353; found 354 [M+H]+, tR=2.84 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 8.13 (d, J=8.2 Hz, 2H), 8.04 (d, J=8.0 Hz, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H), 7.13 (s, 1H), 7.05 (m, 2H), 3.82 (m, 5H).

Provenance & Evidence