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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1747373Generated: November 3, 2026

Water → (S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl ester

https://huagongshe.com/reaction/1747373

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant1-Fluoro-2-nitrobenzeneHCID 73895—
ReactantDiisopropylethylamineHCID 81531—
ReactantEthyl (3S)-3-aminohexanoateHCID 10773249—
SolventDimethylformamideHCID 6228—
Product(S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl esterHCID 5949756681%

Reaction Steps

To a solution of 1-fluoro-2-nitrobenzene (500 mg, 3.5 mmol) in DMF (150 mL) were added (S)-3-Amino-hexanoic acid ethyl ester (600 mg, 3.8 mmol) and diisopropyl ethylamine (0.65 mL, 3.8 mmol). The solution was heated to 90 C for 16 hours. The solution was cooled down and was water (300 mL) was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The mixture was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-(2-Nitro-phenylamino)-hexanoic acid ethyl ester (795 mg, 80%) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150556B2
Source datasetuspto-grants-2015_10
ORD IDord-077cb6fd19544d829273c2e7739df948
Source noteuspto-grants-2015_10