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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2045567Generated: October 31, 2026

4-Fluorobenzoyl chloride → Methyl 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

https://huagongshe.com/reaction/2045567

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Fluorobenzoyl chlorideHCID 67879—
ReactantDiisopropylethylamineHCID 81531—
ReactantMethyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateHCID 67441380—
SolventDichloromethaneHCID 6344—
ProductMethyl 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateHCID 6744100937%

Reaction Steps

To a solution of methyl 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (70 mg, 0.23 mmol) and N,N-diisopropylethylamine (0.09 mL, 0.52 mmol,) in dichloro methane (5 mL) was added 4-fluorobenzoyl chloride (54 mg, 0.34 mmol). The resultant mixture was stirred at room temperature for 16 hrs under nitrogen. The solvent was removed in vacuo and the residue was washed with dichloromethane/petroleum ether, the precipitate was collected to afford methyl 2-(4-(4-fluorobenzamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid, 43 mg, yield: 37%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08586747B2
Source datasetuspto-grants-2013_11
ORD IDord-340d30ec0ebd430faaa46352fbfdd1c6
Source noteuspto-grants-2013_11