Potassium Carbonate → HCID 23130570, compound

HRID 2080149Notes

Reaction equation

HRID 2080149 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Br>CN(C)C=O.[Cl-].[Na+].O>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 27347202-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 23130570HCID 23130570, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-cyanophenol (5 g, 42 mmol) in N,N-dimethyl formamide (40 mL) were added potassium carbonate (17.4 g, 126 mmol) and 2-picolyl bromide hydrobromide (10.6 g, 42 mmol), and the solution was stirred at room temperature for 15 hours. The reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The fractionated organic layer was dried over anhydrous magnesium sulfate, then, filtered by NH silica gel lined over a glass filter, and the filtrate was concentrated to obtain the title compound (4.7 g, 22.4 mmol, 53%).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe fractionated organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered by NH silica gel
  4. filtrationfilter
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5689cbb783324614a6822af4c816c801
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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