Hydrochloric Acid → 2-Phenyl-1-pyridin-3-yl-ethanone

HRID 1579117Notes

Reaction equation

HRID 1579117 reaction equation
CO[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.COC(=O)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+].Cl>C(Cl)(Cl)Cl.O>[CH2:14]([C:3]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7151Methyl NicotinateHCID 7559Methyl phenylacetateHCID 10942334Sodium Methoxide

Product 1

HCID 43289002-Phenyl-1-pyridin-3-yl-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 27.4 g (0.2 mol) of nicotinic acid methyl ester and 30 g (0.2 mol) of phenylacetic acid methyl ester is treated in small amounts under nitrogen with 16.2 g (0.3 mol) of sodium methylate at 20°-25°C. The reaction mixture is stirred for 20 hours at 60°-70°C, in the process of which the alcohol which is formed is blown off. Then 60 ml of concentrated hydrochloric acid is added dropwise to the solid substance and the mixture is boiled for 3 hours under reflux. The still hot yellow solution is treated with 30 ml of water and cooled to 50°C. Then 60 ml of chloroform are added and the reaction mixture is cooled to 5°C. The white crystals which form are collected by suction filtration and washed with chloroform; they melt at 225°C (from ethanol).

Workup

  1. customis formed
  2. temperatureunder reflux
  3. temperaturethe reaction mixture is cooled to 5°C
  4. filtrationThe white crystals which form are collected by suction filtration
  5. washwashed with chloroform
  6. custommelt at 225°C

Sources & evidence

ORD record
ord-5b9dd38d583c4bd3aee27f4c76f760e7
Source dataset
uspto-grants-1976_02
Patent number
US03940486

Reaction notes

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