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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 735246Generated: October 30, 2026

Hexane → 3-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

https://huagongshe.com/reaction/735246

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHexaneHCID 8058—
ReactantSodium hydrideHCID 24758—
ReactantLithium HexamethyldisilazideHCID 2733832—
Reactant2-[2-(4-Bromo-phenyl)-propionylamino]-4,6-dichlorobenzoic acid methyl esterHCID 68816564—
SolventEthyl AcetateHCID 8857—
Product3-(4-bromo-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dioneHCID 1156036218%

Reaction Steps

The objective compound was prepared by the same procedure for the example 1, using a 2-[2-(4-bromo-phenyl)-propionyl amino]-4,6-dichloro-benzoic acid methyl ester (400 mg, 0.93 mmol) and NaH (78 mg, 1.95 mmol) as a base instead of LiHMDS. After normal workup, the objective compound (60 mg, 18%) was obtained as white solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3+CD3OD) δ 1.69 (s, 3H, CH3), 6.91-7.48 (m , 6H, ArH); m.p. 237-238° C.; MS(EI) m/e 397 [M+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07592457B2
Source datasetuspto-grants-2009_09
ORD IDord-8ee734c2109340dda1f22ffd2c677d28
Source noteuspto-grants-2009_09