Butyryl chloride → HCID 178454517, compound

Participants

Reaction Steps

Into the solution of the amine 4 (915 mg, 3.0 mmol) in pyridine (15 mL) was added dropwise butyryl chloride (477 mg, 4.5 mmol), and the reaction was stirred overnight at room temperature. The solvent was evaporated, the residue dissolved in chloroform, washed with hydrochloric acid (1.0 M), water and brine, and dried with magnesium sulfate. Silica gel chromatography with chloroform as eluent gave pure 10 (916 mg, 90%) as orange crystals. 1H NMR (360 MHz, CDCl3): δ 8.19 (d, J=8.4 Hz, 2H), 7.96-7.91 (m, 4H), 7.44 (d, J=8.0 Hz, 2H), 5.86 (br s, 1H), 4.55 (d, J=6.0 Hz), 3.97 (s, 3H), 2.56 (t, J=7.6 Hz, 2H), 1.73 (q, J=7.6 Hz, 2H), 0.99 (t, J=7.6 Hz, 3H). 13C NMR (100.61 MHz, CDCl3): δ 172.55, 166.14, 154.70, 151.49, 141.99, 131.44, 130.22, 128.06, 123.11, 122.26, 51.95, 42.77, 38.29, 18.78, 13.42. HRMS (m/z): [M+H]+ calcd. for C19H21N3O3 340.1656. found 340.1669.

Provenance & Evidence