HCID 11051935, compound → HCID 23653020, compound

Participants

Reaction Steps

1-formyl-imidazole (about 0.100 grams) was dissolved in 1 mL of tetrahydrofuran at room temperature. Immediately, 1 equivalent (eq.) of n-butyl lithium in about 1.6 M (molar) hexanes was added to the reaction mixture, followed by 1.2 eq. of freshly prepared 1:1 molar mixture of potassium nitrate (KNO3) and trifluoroacetic anhydride (TFAA) in tetrahydrofuran as solvent at about 0° C. to about 4° C. The active nitrating species (CF3C(O)ONO2), thus, was generated in situ and the reaction mixture was stirred further for about 1.5 minutes. The 1-formyl-2-nitro-1H-imidazole product was isolated and purified by flash column chromatography to yield the pure product (i.e., about 95% purity) in about 62% yield. The structure of the 1-formyl-2-nitro-1H-imidazole product was confirmed by 1H NMR spectroscopy. 1H NMR (CDCl3): δ 2.8 (s, 3H), 7.20 (d, 1H), 7.74 (d, 1H).

Provenance & Evidence