Pyridine → HCID 178527122, compound

Participants

Reaction Steps

Thionyl chloride (0.55 mL, 7.5 mmol) was added dropwise to a mixture of N'-hydroxy-(1-chloro-3,4-dihydro-2-naphthalenyl)ethanimidamide (1.6 g, 6.8 mmol) and pyridine (1.10 mL, 13.6 mmol) in dry CH2Cl2 (25 mL) at 0° C. After the addition, the reaction was concentrated under reduced pressure, diluted with water (50 mL), and extracted with ether (3×50 mL). The organics were washed with brine, dried (MgSO4), and concentrated to obtain a black froth. The froth was chromatographed on silica gel (twice: eluant 4% MeOH/CH3Cl2 and eluant 2% MeOH/CH2Cl2) to yield 612 mg (32%) of an off-white solid, m.p. 90.5°-91.5° C.

Provenance & Evidence