2-Chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde oxime → 7-Chloro-3-(2-chlorophenyl)-2,6-naphthyridine 2-oxide

HRID 468851Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[CH:9][N:10]=1)[CH:5]=[N:6][OH:7]>C(Cl)(Cl)Cl.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]([CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N+:6]([O-:7])=[CH:5]2)=[CH:9][N:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde oxime (235 mg, 0.81 mmol) and silver nitrate (˜10 wt. % on silica gel, +230 mesh, 275 mg, 0.16 mmol) in chloroform (7 mL) was heated at 60° C. for 1 hour. The cooled reaction mixture was treated with silica gel (1 g), concentrated in vacuo, and purified by flash chromatography (silica, 12 g, ISCO, 0-90% ethyl acetate in heptane) to afford the title compound as pale yellow solid (200 mg, 80%).

Workup

customThe cooled reaction mixture
additionwas treated with silica gel (1 g)
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica, 12 g, ISCO, 0-90% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-dc0e68747525493f8871db944de461e0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623889B2

Reaction notes

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