Benzyl Bromide → 5-Amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one

Participants

Reaction Steps

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (1 g) is alkylated using benzyl bromide (0.46 ml; 3.9 mmol) and K2CO3 (1.5 g; 10.9 mmol) at RT for 20 h. After filtration and evaporation of the solvent the crude material is de-acetylated under reflux conditions in 2-propanol (10 ml) and hydrochloric acid (6 N, 30 ml). Pure 5-amino-1-benzyl-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (1.04 g) precipitates by pouring the reaction mixture into ice-water.

Provenance & Evidence