Trifluoroacetic acid → HCID 67083717, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL round bottom flask charged with a magnetic stir bar was added TFA (30 mL). The flask was cooled to 0° C. in an ice bath and ethyl 3-{4,5-dimethoxy-2-[(E)-pyrrolidin-1-yldiazenyl]phenyl}-3-oxopropanoate sodium salt (4.03 g, 10.83 mmol) (Method 3) was added to the reaction mixture in portions over 10 minutes. The mixture was stirred at this temperature for an additional 2 h before being poured over 0° C. ice-water (˜300 mL). The desired product precipitated from the mixture and was collected via vacuum filtration using a Buchner funnel. The solid was rinsed with water (1×100 mL) and diethyl ether (1×100 mL) to yield 1.55 g (51%) of the title compound as an off white solid that was used without further purification. 1H NMR: 13.70 (s, NH, 1H), 7.39 (s, 1H), 7.00 (s, 1H), 4.30 (q, 2H), 3.95 (s, 3H), 3.89 (s, 3H), 1.30 (t, 3H); m/z 279.

Provenance & Evidence