Potassium Hydroxide → HCID 69053921, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 1-((4-methoxy-2,3-dimethylphenylamino)methyl)-cyclobutanecarboxylate (19 g) in ethanol (120 mL) was added KOH (9 g in 50 mL of water). The solution was then heated up in an 85° C. bath for 2 hours. The solution was then evaporated to dryness, HCl (3 M) was then added while the flask cooled in ice bath to reach a pH of less than 1, and the solution was extracted with ethylacetate. The combined organic phases were then dried and evaporated to give 1-((4-methoxy-2,3-dimethylphenylamino)methyl)cyclobutanecarboxylic acid (21.0 g), which was used in the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ=8.78-7.95 (s, 1H), 6.81-6.74 (d, 1H), 6.73-6.66 (d, 1H), 3.77 (s, 3H), 3.44 (s, 2H), 2.68-2.41 (m, 2H), 2.17 (s, 3H); 2.14 (s, 3H), 2.09-1.93 (m, 4H) ppm. 13C-NMR (75 MHz, CDCl3) δ=181.21, 15.251, 137.65, 126.32, 125.78, 112.31, 108.99, 56.21, 52.84, 46.64, 28.46, 15.93, 13.36, 12.27 ppm.

Provenance & Evidence