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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1721181Generated: November 1, 2026

Ethyl Acetate → 4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid

https://huagongshe.com/reaction/1721181

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant3-AminophenolHCID 11568—
ReactantSodium hydrideHCID 24758—
Reactant2-Chloromethyl-7-acetyl-quinolineHCID 22416851—
Reactant3-(7-Acetyl-2-quinolinylmethoxy)anilineHCID 22416922—
SolventDimethylformamideHCID 6228—
Product4-[3-(7-Acetyl-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acidHCID 22416914—

Reaction Steps

3-(7-acetyl-2-quinolinylmethoxy)aniline: 30 mg of NaH (95%) are added at 0° to a solution of 0.13 g of 3-aminophenol in 2.5 ml of DMF and then the batch is stirred for 30 min. at 0°. 0.25 g of 2-chloromethyl-7-acetyl-quinoline in solid form is then added and the batch is stirred for a further one hour at 0° and for another hour at 20°. It is then diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated by evaporation. The evaporation residue is chromatographed on 25 g of silica gel. The product-containing fractions eluted with toluene/ethyl acetate 85:15 are combined and concentrated by evaporation to give the title compound which is further reacted directly.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05508408
Source datasetuspto-grants-1996_04
ORD IDord-7fd1b0716a154950adb94f29f3060f37
Source noteuspto-grants-1996_04