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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 584639Generated: October 28, 2026

4-Chloroaniline → HCID 22313565, compound

https://huagongshe.com/reaction/584639

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 numberUS06927222B2
Source datasetuspto-grants-2005_08
ORD IDord-2e6859bb30924dde8da38b9af94dc9a0
Source noteuspto-grants-2005_08