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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1642351Generated: October 25, 2026

2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehyde → Pyrvinium Pamaote Impurity 3

https://huagongshe.com/reaction/1642351

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,5-Dimethyl-1-phenylpyrrole-3-carboxaldehydeHCID 66515—
Reactant6-Quinolinamine, N,N,2-trimethyl-HCID 66725—
CatalystZincchlorideHCID 3007855—
SolventDimethylformamideHCID 6228—
SolventSodium HydroxideHCID 14798—
ProductPyrvinium Pamaote Impurity 3HCID 250157752.1%

Reaction Conditions

Temperature160 °C

Reaction Steps

To a solution of compound 3 (316 mg, 1.7 mmol) and compound 5 (507 mg, 2.55 mmol) in DMF (25 mL) was added ZnCl2 (232 mg, 1.7 mmol). The reaction mixture was stirred at 160° C. overnight. Then the reaction mixture was diluted with aqueous NaOH (10%) and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure, the residue was purified by column chromatography (hexane:EtOAc=20:1) to give 13 mg of the target product (2.1%). MS[M++1]=368, LC-MS: tR=1.909 min

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119660B2
Source datasetuspto-grants-2012_02
ORD IDord-5d24bac05cac4800a7e07b766a4fb763
Source noteuspto-grants-2012_02