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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1693858Generated: October 27, 2026

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

https://huagongshe.com/reaction/1693858

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 numberUS08158657B2
Source datasetuspto-grants-2012_04
ORD IDord-3de07807053148e6a1088d4912a13197
Source noteuspto-grants-2012_04