Ethyl Acetate → HCID 23506255, compound

HRID 1267937Notes

Reaction equation

HRID 1267937 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]([C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:10]([C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1)#[N:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 23506255HCID 23506255, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

2-Bromo-3-methoxypyridine (15 g, 68 mmol) and 3-cyanophenol (8.9 g, 75 mmol) are dissolved in DMF (150 ml), and thereto are added potassium carbonate (28 g, 0.2 mol) and cuprous bromide (10.7 g, 75 mmol), and the mixture is heated under reflux at 140° C. for 1.5 hours. After being allowed to cool, to the reaction solution is added ethyl acetate (1000 ml), and the mixture is washed with a saturated brine (200 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from isopropyl ether/hexane to give the title compound (11.1 g) as pale brown crystals, m.p. 88-89° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto cool, to the reaction solution
  3. washthe mixture is washed with a saturated brine (200 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is recrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-92ab59c4abc44fab8753728359b6a202
Source dataset
uspto-grants-2003_04
Patent number
US06555557B1

Reaction notes

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