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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1818910Generated: November 2, 2026

Triphenylphosphine → 2-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one

https://huagongshe.com/reaction/1818910

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
Reactantethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Reactant4-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamideHCID 66803630—
SolventTetrahydrofuranHCID 8028—
Product2-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-oneHCID 1128863491.2%

Reaction Conditions

Temperature0 °C

Reaction Steps

4-(2-hydroxy-ethyl)-N-(4-methoxy-benzyl)-nicotinamide (2.2 g, 7.683 mmol) and triphenylphosphine (4.03 g, 15.37 mmol) were dissolved in 50 mL of anhydrous THF. The mixture, while being stirred at 0° C. under the nitrogen atmosphere, dropwisely added with diethyl azocarboxylate (1.4 mL, 9.220 mmol) and stirred for about 1 hour at room temperature. The mixture was then concentrated under reduced pressure and a silica gel column chromatography (3% MeOH/MC) was performed on the resulting residue and obtained 1.88 g (91%) of 2-(4-methoxy-benzyl)-3,4-dihydro-2H-[2,7]naphtyridine-1-on in white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07601736B2
Source datasetuspto-grants-2009_10
ORD IDord-1e9c0e1ac9fa4f8790d1b67610e97c34
Source noteuspto-grants-2009_10