(NE)-N-(4-bromo-2,3-dihydroinden-1-ylidene)hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2,3-dihydro-1H-inden-1-one (3.00 g, 14.21 mmol) in MeOH (40 mL) was added hydroxylamine hydrochloride (3.95 g, 56.9 mmol). The resulting mixture was refluxed for 1 h and concentrated in vacuo. The resulting residue was partitioned between DCM and 50% saturated NaHCO3, and stirred vigorously for 20 min. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound (3.18 g, 99% yield) as a pale yellow solid. LCMS, [M+H]+=226.0. The resulting mixture was refluxed for 1 h concentrated in vacuo The resulting residue was partitioned between DCM and 50% saturated NaHCO3 The organic layer was separated dried over anhydrous Na2SO4 filtered concentrated