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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891621Generated: October 30, 2026

Acetic Acid → 5-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

https://huagongshe.com/reaction/1891621

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantNitromethaneHCID 6375—
ReactantAmmonium AcetateHCID 517165—
Reactant4-(5-Methyl-pyridin-2-yloxymethyl)-benzaldehydeHCID 59255142—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Product5-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridineHCID 59255428100.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

To an acetic acid (20.0 mL) solution of 4-(5-methyl-pyridin-2-yloxymethyl)-benzaldehyde (2.93 g, 12.9 mmol) described in Manufacturing Example 44-1-2 were added nitromethane (3.94 g, 64.5 mmol) and ammonium acetate (1.99 g, 25.8 mmol under nitrogen atmosphere at room temperature, which was stirred for 2.5 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. This organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.50 g) as a crude product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507530B2
Source datasetuspto-grants-2013_08
ORD IDord-3e458e2ade1240f5a45776f78db66850
Source noteuspto-grants-2013_08