Hydroxylamine sulfate → HCID 22462506, compound

Participants

Reaction Conditions

Reaction Steps

The mixture that consists of 6-nitro-2,3,3a,8a-tetrahydro-1H-cyclopentta]inden-8-one and 5-methyl-6-nitro-2,3,3a,8a-tetrahydro-1H-cyclopent[a]inden-8-one (3.76 g) is dissolved with hydroxylammonium sulfate (5.58 g, 34 mmol) and sodium acetate (9.25 g, 68 mmol) in THF-ethanol-water 1:1:1 (180 ml). The batch is stirred for 6 hours at 60° C., left for three days at room temperature, concentrated by evaporation, diluted with ether, washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is purified on silica gel with the eluant ether-hexane. Yield: 3.76 g; the oxime mixture is dissolved at 120° C. in polyphosphoric acid. The batch is stirred for four hours at 120° C., it is poured onto ice water after cooling and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is prepurified on silica gel with ethyl acetate-hexane, and the mixture is then separated using preparative HPLC (LC.50 Novapak column, eluant: methanol-aqueous ammonium acetate solution):

Provenance & Evidence