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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1173885Generated: October 27, 2026

Acetic Acid → 2-{4-[(4-Dipropylaminomethylphenylamino)methyl]benzyl}isoindole-1,3-dione

https://huagongshe.com/reaction/1173885

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant4-Dipropylaminomethyl-anilineHCID 16777011—
Reactant4-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)benzaldehydeHCID 23155547—
SolventMethanolHCID 887—
SolventWaterHCID 962—
Product2-{4-[(4-Dipropylaminomethylphenylamino)methyl]benzyl}isoindole-1,3-dioneHCID 21084376250.1%

Reaction Steps

The compound (17.6 mg) obtained in Example 25-1, the compound (13.2 mg) obtained in Example 19-2, and sodium cyanoborohydride (8.7 mg) were dissolved in anhydrous methanol (1.0 ml). The solution was then adjusted to pH 5 with the addition of acetic acid, followed by stirring at room temperature for 4 hours. The reaction solution was added with distilled water and then subjected to extraction with chloroform. After that, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel preparative thin-layer chromatography (chloroform/methanol), thereby obtaining the subject compound (72.9 mg) as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07833991B2
Source datasetuspto-grants-2010_11
ORD IDord-b707b18300b640c9a6709d8d62fd68b7
Source noteuspto-grants-2010_11