Potassium Iodide → HCID 23312310, compound

HRID 2401685Notes

Reaction equation

HRID 2401685 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.Cl.Cl[CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C=O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:4][C:3]=2[CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 23312310HCID 23312310, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 0.64 g of 2-hydroxy-5-methoxybenzaldehyde, 0.72 g of 4-(chloromethyl)pyridine hydrochloride, 1.74 g of potassium carbonate, 0.70 g of potassium iodide and 15 ml of DMF was stirred at 80° C. for 3 hours and subsequently at 150° C. for 6 hours. The reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over sodium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.60 g of 4-(5-methoxybenzofuran-2-yl)pyridine (hereinafter, referred to as “Present Active Compound 2”).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38a630520adb46a6ab6b8d59417cdb3c
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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