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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1593418Generated: October 29, 2026

Sodium Methoxide → 5-{(E)-3-[4-(2-Dimethylamino-ethoxy)-phenyl]-3-oxo-propenyl}-indan-1-one O-methyl oxime

https://huagongshe.com/reaction/1593418

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium MethoxideHCID 10942334—
Reactant1-[4-(2-Dimethylaminoethoxy) phenyl]ethanone hydrochlorideHCID 12214393—
Reactant1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-HCID 73012344—
SolventMethanolHCID 887—
SolventWaterHCID 962—
Product5-{(E)-3-[4-(2-Dimethylamino-ethoxy)-phenyl]-3-oxo-propenyl}-indan-1-one O-methyl oximeHCID 8659541083%

Reaction Steps

A solution of the product of Example 1 Step 2 (1.06 g, 5.6 mmol), sodium methoxide (0.750 g, 13.9 mmol) and 1-[4-(2-dimethylaminoethoxy) phenyl]ethanone hydrochloride (1.36 g, 5.6 mmol) (J. H. Short et al., J. Med. Chem. 1965, 8, 223) in methanol (30 ml) and water (1 ml) was heated under reflux for 5 hours. After cooling to room temperature the solid was collected, washed with cold methanol and diethyl ether and dried to give the title compound (1.74 g, 83%); MS(ES+) m/e 378 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07297694B2
Source datasetuspto-grants-2007_11
ORD IDord-887006bc5cfb46bda350c6df0b00d21a
Source noteuspto-grants-2007_11