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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1844004Generated: October 30, 2026

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

https://huagongshe.com/reaction/1844004

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantTriphenylphosphineHCID 11776—
ReactantDiethyl azodicarboxylateHCID 5462977—
Reactant4-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamideHCID 66803630—
SolventChloroformHCID 6212—
SolventTetrahydrofuranHCID 8028—
Product2-(4-methoxybenzyl)-3,4-dihydro-2,7-naphthyridin-1(2H)-oneHCID 1128863449.82%

Reaction Steps

DEAD (1.094 g, 6.286 mmol) was added drop wise to a solution of 4-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamide (I-65d: 1.5 g, 5.238 mmol) and PPh3 (2.784 g, 10.477 mmol) in THF (40 mL) at 0° C. and the resulting reaction mass was stirred at room temperature for 1 hour. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was concentrated under reduced pressure and the crude residue was purified by column chromatography on silica gel (3% methanol in DCM) to afford 700 mg of the product (49.82% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946260B2
Source datasetuspto-grants-2015_02
ORD IDord-eae0d287df6e42b8a05111af28ca3d4d
Source noteuspto-grants-2015_02