Hydrochloric Acid → HCID 21469301, compound

Participants

Reaction Conditions

Reaction Steps

The above 3-amino-7-benzyloxyquinoline (2.3 g, 9.2 mmol.) was dissolved in a mixture of acetone and water (25 mL and 6 mL). Under chilling with ice, to the solution was added concentrated hydrochloric acid (2.5 mL). The reaction temperature was set to a temperature of lower than 5° C. The reaction mixture was stirred at 5° C. for 20 minutes after addition of aqueous sodium nitrite solution (833 mg (12 mmol.)/1.6 mL) for 5 minutes. After the stirring was complete, methyl acrylate (6 mL, 67.5 mmol.) was added for 5 minutes. Then, cuprous oxide (120 mg) was gradually added, and the reaction temperature was set to 37° C. Under the condition, the reaction mixture was vigorously stirred. After the completion of reaction was confirmed, acetone was distilled off. To the residue were added ethyl acetate and concentrated aqueous ammonia, so that the aqueous portion reached pH 7. The organic portion was recovered, washed with water, and dried over anhydrous sodium sulfate. The dried mixture was filtered, and the filtrate was placed under reduced pressure to distill off ethyl acetate. The residue was purified by column chromatography (hexane/ethyl acetate=2/1), to give 1.65 g of the desired compound as a pale yellowish white crystalline product (yield 51%).

Provenance & Evidence