Formaldehyde → HCID 22380815, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine and 3-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine in 37% formaldehyde (5 mL) in a sealed tube is heated at 150° C. overnight. The mixture is allowed to cool to ambient temperature and evaporated under reduced pressure. The resulting residue is partitioned between ethyl acetate and water and the layers are separated. The aqueous layer is further extracted with ethyl acetate and the combined organic extracts are dried over Na2SO4, filtered and the solvents removed under reduced pressure. Column chromatography of the residue on silica gel (5% MeOH in CH2Cl2 as eluent) gives [1-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo [4,5-c]pyridin-2-yl]-methanol (80 mg). 1H NMR (CDCl3) δ: 8.33 (d, 1H), 8.15 (dd, 1H), 6.73 (q, 1H), 4.64 (s, 2H), 4.22 (s, 2H), 3.90-3.98 (m, 4H), 2.82(t, 2H) and 1.36 (t, 3H). MS: 304.2 (m+1).

Provenance & Evidence