Hydrochloric Acid → HCID 67125571, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylbenzoate 103 (7.13 mmol, 2.5 g) in THF (30 mL), lithium hydroxide (28.5 mmol, 0.683 g) in (20 mL) water was added and the reaction was stirred overnight at 40° C. The reaction mixture was acidified with 2N HCl solution and extracted with ethyl acetate (2×). Organic layer was washed with 2N NaOH (3×), aqueous layer was acidified with 2N HCl solution and the milky mixture was extracted with ethyl acetate (3×), dried and concentrated under reduced pressure. Crude product was triturated with ACN to give 5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylbenzoic acid 104 (550 mg, 23%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.50 (s, 3H), 7.30 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.4 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.90 (dd, J=8.2 Hz and 2.3 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (t, J=2.0 Hz, 1H), 8.24 (d, J=2.3 Hz, 1H), 10.40 (s, 1H). (m/z)=323 (M+H)+.

Provenance & Evidence