2-Chloro-3-nitropyridine → 3-Nitro-2-phenoxypyridine

HRID 1352525Notes

Reaction equation

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

Participants

Reactant 2

HCID 796132-Chloro-3-nitropyridine

HCID 4445035Phenolate Sodium

Product 1

HCID 9018963-Nitro-2-phenoxypyridine

Procedure

In step (6) of Reaction Scheme II, a 2-chloro-3-nitropyridine of Formula XXV is reacted with sodium phenoxide to provide a 3-nitro-2-phenoxypyridine of Formula XXVI. Phenol is reacted with sodium hydride in a suitable solvent such as tetrahydrofuran to form the phenoxide. The phenoxide is then reacted at an elevated temperature with a compound of Formula XXV.

Workup

customIn step (6) of Reaction Scheme II

Sources & evidence

ORD record: ord-566677fea97f4ee598fbde8ca22f3712
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220758B2

Reaction notes

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