Sodium Hydroxide → HCID 22501979, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium borohydride (193 mg, 5.12 mmol) in ethanol (4 ml) was added dropwise to a stirred solution of 2-isopropyl-5-nitro-isoindole-1,3-dione (1.20 g, 5.12 mmol) and tin (II) dichloride dihydrate (3.47 g, 15.36 mmol) in ethanol (40 ml) at 60° C. The resulting solution was stirred for 2 hrs, after which time the reaction was cooled to 0° C. and basified using 2M sodium hydroxide. The aqueous phase was extracted with dichloromethane (3×20 ml) and the combined organics washed with brine, then dried (MgSO4) and evaporated in vacuo. The crude residue was purified by preparative HPLC (Method D) to afford the title compound as a yellow solid (512 mg, 49%). HPLC retention time 7.2 min. Mass spectrum (ES+) m/z 205 (M+H).

Provenance & Evidence