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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 496218Generated: October 31, 2026

4-Chloroaniline → HCID 22313565, compound

https://huagongshe.com/reaction/496218

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-ChloroanilineHCID 7812—
Reactant1-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 379000—
ReactantSodium BicarbonateHCID 516892—
ReactantSodium triacetoxyborohydrideHCID 5049666—
SolventAcetic AcidHCID 176—
Solvent1,1-DichloroethaneHCID 6365—
SolventEthyl AcetateHCID 8857—
ProductHCID 22313565HCID 2231356594.3%

Reaction Steps

Tert.butyl-2-oxo-1-pyrrolidinecarboxylate (190 mg, 1.02 mmol), 4-chloroaniline (64 mg, 0.5 mmol) and acetic acid (184 mg) were mixed in dichloroethane (5 mL). Sodium triacetoxyborohydride (326.5 mg) was added and the reaction mixture kept on stirring at room temperature for overnight. After addition of aq. NaHCO3 the reaction mixture was diluted by addition of ethyl acetate. Two layers were separated. The organic layer was dried over Na2SO4, filtered, concentrated. The residue was purified by flash chromatography (0-15% ethyl acetate in petroleum spirit, 40-60) to give the subtitled product (140 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06943188B2
Source datasetuspto-grants-2005_09
ORD IDord-a3b7a3564b934c74a6246a42258714a5
Source noteuspto-grants-2005_09