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

HRID 641810

Reaction equation

HRID 641810 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=[CH:11][C:4]=2[N:3]=1.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=O>CN(C=O)C.[OH-].[Na+].[Cl-].[Cl-].[Zn+2]>[CH3:14][N:12]([CH3:13])[C:9]1[CH:8]=[C:5]2[C:4](=[CH:11][CH:10]=1)[N:3]=[C:2](/[CH:1]=[CH:21]/[C:20]1[CH:19]=[C:18]([CH3:23])[N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]=1[CH3:15])[CH:7]=[CH:6]2

Participants

6

Reactant 2

HCID 665152,5-Dimethyl-1-phenylpyrrole-3-carboxaldehydeHCID 667256-Quinolinamine, N,N,2-trimethyl-

Product 1

HCID 25015775Pyrvinium Pamaote Impurity 3Yield 2.1%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
160 °C

Procedure

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

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography (hexane: EtOAc=20:1)

Sources & evidence

ORD record
ord-542751499db846c49ec3256d8634c523
Source dataset
uspto-grants-2010_04
Patent number
US07696227B2

Linked notes

Loading…