Hydrochloric Acid → HCID 10564937, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4.8 g (0.0124 mol) of 1-benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole prepared as in Part A hereof in 200 mL of THF cooled to -78° C. under N2 atmosphere, were added 16 mL (0.025 mol) of 1.6 M solution of n-butyl-lithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes and then allowed to warm to -20° C. To the reaction mixture was added 100 mL of 1 N HCl. The mixture was extracted once with ethyl ether. The acidic solution was made alkaline with the addition of cold 5 N NaOH. The basic mixture was extracted twice with CH2Cl2. The combined organic solution was washed with saturated aqueous NaCl solution. The CH2Cl2 solution was dried over MgSO4 and evaporated to give 4 g of an oil. Chromatography of this oil over silica gel with ethyl acetate as eluent gave 3 g (85%) of product as an oil, which upon standing solidified.

Provenance & Evidence