3-Pyridinecarboxaldehyde → HCID 19775361, compound

HRID 1613147Notes

Reaction equation

HRID 1613147 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Mg].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]Br)=[CH:13][CH:12]=1.[NH4+].[Cl-]>C(OCC)C.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:8])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 5731534-Fluorophenethyl bromideHCID 5462224Magnesium

Product 1

HCID 19775361HCID 19775361, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 10.7 g (0.10 mole) of nicotinaldehyde in 100 ml of diethyl ether is added dropwise, while stirring, to a solution prepared from 2.92 g (0.12 mole) of magnesium and 24.4 g (0.12 mole) of 2-(4-fluorophenyl)-ethyl bromide in 250 ml of diethyl ether, and the mixture is then refluxed for 2 hours. Cooling is followed by hydrolysis with water, and the pH is brought to 8 with saturated aqueous NH4Cl solution. The phases are separated, the aqueous phase is extracted twice more with ether, and the combined organic phases are washed with water and dried over NgSO4. The solvent is evaporated off and the residue is distilled under reduced pressure to give 10.2 g (44% of theory) of compound No. 4 of boiling point 190° C. (2 mbar).

Workup

  1. temperaturethe mixture is then refluxed for 2 hours
  2. temperatureCooling
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted twice more with ether
  5. washthe combined organic phases are washed with water
  6. customdried over NgSO4
  7. customThe solvent is evaporated off
  8. distillationthe residue is distilled under reduced pressure
  9. customto give 10.2 g (44% of theory) of compound No

Sources & evidence

ORD record
ord-025ed52354ab4120948b789192039683
Source dataset
uspto-grants-1993_03
Patent number
US05192767

Reaction notes

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