Water → HCID 21076641, compound

Participants

Reaction Conditions

Reaction Steps

6-Acetyloxyhexanoic acid chloride (16.7 g, 86.6 mmol) in absolute CH2Cl2 (50 ml) is added in drops at 0° C. within 10 minutes to a suspension of anhydrous aluminum chloride (61.5 g, 461.6 mmol) in absolute CH2Cl2 (500 ml), and it is stirred for 15 minutes at this temperature. 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-one (10.0 g (57.7 mmol) in absolute CH2Cl2 (100 ml) is added in drops within 15 minutes at 0° C., then it is heated to boiling temperature and stirred for 30 minutes. It is cooled to 0° C., hydrolyzed with ice and dispersed between water (300 ml) and CH2Cl2 (100 ml). The aqueous phase is extracted with CH2Cl2 (2×100 ml), the combined organic phases are washed with 2N hydrochloric acid (2×250 ml), water (2×250 ml), semi-concentrated aqueous Na2CO3 solution (2×250 ml), concentrated aqueous Na2CO3 solution (2×250 ml) and concentrated common salt solution (1×250 ml), dried (sodium sulfate/activated carbon), and the solvent is removed in a rotary evaporator.

Provenance & Evidence