4-Methyloxybenzyl chloride → 5-Chloro-1-(4-methoxy-benzyl)-3-nitro-1H-pyridin-2-one

HRID 869075Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[N:6]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH:7]=1

Participants

Reactant 2

HCID 699934-Methyloxybenzyl chloride

HCID 178526657HCID 178526657, compound

Product 1

HCID 896013295-Chloro-1-(4-methoxy-benzyl)-3-nitro-1H-pyridin-2-one

Conditions

Temperature: 80 °C

Procedure

The title compound was prepared in analogy to the procedure described for example 1 but using 5-chloro-3-nitropyridin-2-ol and 4-methoxybenzyl chloride. The reaction was stirred for 1 h at 80° C. The residue was purified by silica gel column chromatography (CH2Cl2/EtOAc, 8:2). tR: 0.91 min (LC-MS 4); ESI-MS: 295.2 [M+H]+ (LC-MS 4); Rf=0.59 (hexane/EtOAc, 1:1).

Workup

customThe residue was purified by silica gel column chromatography (CH2Cl2/EtOAc, 8:2)

Sources & evidence

ORD record: ord-527adba788d54f73a05c2cbec902b596
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969341B2

Reaction notes

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