Nitromethane → 4-Chloro-2-methoxy-1-(2-nitroethenyl)benzene

HRID 1021460Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[N+:12]([CH3:15])([O-:14])=[O:13].Cl.CN.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:15]/[N+:12]([O-:14])=[O:13])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

Reactant 4

HCID 6375Nitromethane

HCID 517045Sodium Acetate

HCID 6364545Methylamine hydrochloride

HCID 138651154-Chloro-2-methoxybenzaldehyde

Product 1

HCID 670805334-Chloro-2-methoxy-1-(2-nitroethenyl)benzeneYield 78.3%

Procedure

4-Chloro-2-methoxybenzaldehyde (250 mg, 1.47 mmol) was diluted with nitromethane (556 μL, 10.3 mmol) followed by the addition of methylamine hydrochloride (59.4 mg, 0.879 mmol) and sodium acetate (72.1 mg, 0.879 mmol). After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 cartridge and eluted with 5% ethyl acetate/hexanes to yield (E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol, 78.3% yield).

Workup

washeluted with 5% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-c16118691dfa490db1939ef608f42a4b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716498B2

Reaction notes

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