Acetic Acid → HCID 21072009, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(acetylamino)-2-butyl-2-(3-oxobutyl)-1-indanone (9.8 g, 31.1 mmol) in toluene (300 mL) was treated with pyrrolidine (2.6 mL, 31 mmol) and acetic acid (1.8 mL, 31 mmol). The mixture was stirred under a N2 atmosphere and heated in an oil bath at 90° C. for two hours. After cooling, the mixture was diluted with EtOAc (500 mL), washed with water, 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange-brown foam (7.0 g). 1H NMR of the crude product showed 7-(acetylamino)-9a-butyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one along with 14–17% of a by-product identified as 9a-butyl-4-methyl-8,9,9a,10-tetrahydro-7H-indeno[1,2-g]quinolin-7-one.

Provenance & Evidence