Hydrochloric Acid → HCID 86692165, compound

Participants

Reaction Steps

To a solution of 3-benzyl-1-oxoisoindoline-5-carbonitrile (190 mg, 0.77 mmol) in MeOH (4 mL) was added cobalt(II) chloride hexahydrate (364 mg, 1.53 mmol), then added NaBH4(232 mg, 6.12 mmol) in portions carefully within 45 min. The reaction mixture was stirred at room temperature for 30 min, TLC showed complete conversion. Carefully quenched reaction by adding concentrated HCl until the black precipitates dissolved. The reaction mixture was basified with concentrated NH4OH until pH=8-9, a brown colour slurry was obtained, diluted with ethyl acetate. This was filtered, for filtrate, washed 1× with water. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 5-10% MeOH in dichloromethane (0.5% NEt3 added), 80 mg (41%) of the product was obtained.

Provenance & Evidence