Acetic Acid → HCID 69659346, compound

Participants

Reaction Steps

To a suspension of 3-(6-amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.378 mmole) were added saturated formaldehyde aqueous solution, and sodium cyanoborohydride (300 mg, 4.77 mmole). The resulting mixture was stirred at room temperature for 1 hour, and then was acidified with 10% AcOH aqueous solution. After stirred for another 10 minutes, the reaction was partitioned between CHCl3 and saturated NaHCO3 aqueous solution. The aqueous layer was extracted with CHCl3 (2×5 ml). The combined organic layers were washed with brine, and then dried over anhydrous MgSO4. Removal of the solvent afforded a crude product. Recrystallization of the crude product from MeOH led to 3-(6-dimethylamino-3H-isobenzofuran-1-ylidene)-1-hydroxymethyl-1,3-dihydro-indol-2-one as a yellow solid (90 mg, 74%).

Provenance & Evidence