HCID 118022928, compound → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-4,5-dihydro-1-(3-pyridinyl)-1H-pyrazole (0.182 g, 1.00 mmol) and manganese (IV) oxide (0.870 g, 10.0 mmol) (Carus black) in chlorobenzene (2 mL) was heated at 80° C. for 24 hours. The mixture was allowed to cool to room temperature, filtered through Celite®, and the wetcake was rinsed with chlorobenzene (2 mL). The lightly tinted solution was acidified with hydrochloric acid (4 M in 1,4-dioxane) to ˜pH 1.5 to give a thick, white mixture. After stirring in an ice-bath for 30 minutes, the mixture was filtered through a sintered glass funnel and rinsed with cold chlorobenzene (2 mL). The solids (0.380 g) were allowed to air-dry in a hood overnight to give the title compound as an off-white solid (0.140 g, 64%, LC internal standard analysis indicated a purity of 98.7 wt %): mp 229-237° C.; 1H NMR (DMSO-d6) δ 11.11 (bs, 1H), 9.27 (d, J=2.4 Hz, 1H), 8.82 (d, J=2.7 Hz, 1H), 8.71 (dd, J=5.1, 1.2 Hz, 1H), 8.61 (ddd, J=8.5, 2.5, 1.2 Hz, 1H), 7.89 (dd, J=8.5, 5.1 Hz, 1H), 6.79 (d, J=2.7 Hz, 1H).

Provenance & Evidence