Acetic Acid → HCID 18640897, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-diisopropyl-estr-1,3,5(10)-triene-3-ol-17β-carboxamide (141 mg, 0.368 mmol) in boiling acetic acid (7 mL) was slowly cooled to 75° C. and treated with a solution of concentrated nitric acid (24.8 μL) in water (1.4 mL) containing a catalytic unit of sodium nitrite. The reaction mixture was allowed to slowly cool to room temperature, then was diluted with water and extracted with ethyl acetate. The extract was washed thoroughly with water, dried, concentrated and purified by chromatography (silica gel, dichloromethane containing 5 to 10% ether) affording 55.2 mg (35%, mp 143.5°-144.5° C.) of N,N-diisopropyl-2-nitro-estr-1,3,5(10)-triene-3-ol-17β-carboxamide and 32.2 mg (20%, mp 239°-241° C.) of N,N-diisopropyl-4-nitro-estr-1,3,5(10)-triene-3-ol-17β-carboxamide.

Provenance & Evidence