P-Xylene → HCID 11391343, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of 5-nitroindole (2.0 g, 12.3 mmol) and NaOH pellets (0.49 g, 1 eq) in H2O (2.0 mL) was stirred at RT. After 10 min, p-xylene (15.0 mL, 1.4 M), K2CO3 (2.55 g, 1.5 equ) and N-diethylaminoethyl chloride hydrochloride (2.12 g, 12.3 mmol, 1 eq) was added, and the reaction mixture was heated to 100° C. After 4 h the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude residue was dissolved in p-xylene and washed with 1N NaOH (2×) and H2O (1×). The organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure to afford the nitro compound (1.79 g, 56%). TLC (5% MeOH/EtOAc), Rf=0.25; LC MS m/z 262.2 (MH+).

Provenance & Evidence