HCID 18705862, compound → HCID 18705870, compound

Participants

Reaction Conditions

Reaction Steps

(Ref. Brewster, J. H.; Fusco A. M. J.Org. Chem., 28, 501-503 (1963)) A solution of 6-(dipropylamino)-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione 93 (0.45 g, 1.6 mmol) in glacial HOAc (50 mL) was treated with Zinc dust (1.05 g, 16.0 mmol) then refluxed at 113° C. for 24 h. The reaction was cooled to r.t., diluted with MeOH and filtered through a pad of celite. The filtrate was concentrated and the residue was diluted with H2O, basified with sat'd Na2CO3, and extracted with CH2Cl2. The organic layers were washed with brine, dried (MgSO4), and concentrated. The resulting solid was purified using silica gel, eluting with 2:1 heptane/acetone to give 94 as a white solid (m.p. 206-208° C.).

Provenance & Evidence