Potassium Hydroxide → HCID 22243516, compound

Participants

Reaction Steps

Methyl 6-methyl-isoquinoline-3-carboxylic acid (0.618 g, 3.07 mmol) is dissolved in 95% EtOH (30 mL). KOH pellets (0.517 g, 9.21 mmol) are added and the reaction is heated at reflux for 1 hour. While heating, a precipitate began to form. Upon cooling, this precipitate (the K+ salt) is filtered and dried at 60° C. in vacuo. The precipitate is dissolved in water and the pH is adjusted to 4–5. The water solution is then loaded onto a column of AGW-×2 resin (H+ form). The resin is rinsed with MeOH, and the desired product is eluted with a solution of 5% TEA in MeOH. The product is concentrated three times from MeOH/MeCN and dried in vacuo. The solid is then dried overnight at 60° C. to yield 6-methyl-isoquinoline-3-carboxylic acid (0.41 g, 71%). HRMS (FAB) calculated for C11H8N O2 K: 188.0711, found 188.0714.

Provenance & Evidence