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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 56224Generated: October 27, 2026

But-1-ene-1,3-dione → N-(3-chloro-4-((2-methyl-1-(naphthalen-2-yl)propan-2-yl)amino)phenyl)-3-oxobutanamide

https://huagongshe.com/reaction/56224

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBut-1-ene-1,3-dioneHCID 12642904—
Reactant2-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamineHCID 90031767—
SolventEthyl AcetateHCID 8857—
ProductN-(3-chloro-4-((2-methyl-1-(naphthalen-2-yl)propan-2-yl)amino)phenyl)-3-oxobutanamideHCID 90023565265.8%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of 2-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamine (2.0 g, 6.16 mmol) in EtOAc (30 mL) was added acetyl ketene (1.55 g, 1.84 mmol) and the mixture was stirred at 90° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a white solid (2.00 g, 79%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434695B2
Source datasetuspto-grants-2016_09
ORD IDord-174d1e57cf63495fbcda1a3b04d8a5a9
Source noteuspto-grants-2016_09