Ammonia → 1-(6-Methylpyridin-3-yl)-2-(4-(methylthio)phenyl)ethanone

HRID 413471Notes

Reaction equation

HRID 413471 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](C#N)[C:10]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[O:11])=[CH:5][CH:4]=1.Cl.N>C(O)(=O)C>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 113005426-Methyl-α-[4-(methylthio)phenyl]-β-oxo-3-pyridinepropanenitrile

Product 1

HCID 101313251-(6-Methylpyridin-3-yl)-2-(4-(methylthio)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 8.0 g (28 mmol) of 3-[2-(4-(methylthio)phenyl)-2-cyanoacetyl](6-methyl)pyridine, 20 ml of acetic acid and 60 ml of concentrated hydrochloric acid was heated at 95° C. to 100° C. for 1.5 h. The orange solution was cooled and adjusted to pH 10 using concentrated ammonia solution. The resulting yellow-beige suspension was filtered and the residue was washed with water and dried. This gave 5.35 g (74%) of the title product in the form of a yellow solid.

Workup

  1. temperaturewas heated at 95° C. to 100° C. for 1.5 h
  2. temperatureThe orange solution was cooled
  3. filtrationThe resulting yellow-beige suspension was filtered
  4. washthe residue was washed with water
  5. customdried

Sources & evidence

ORD record
ord-87f0bc21fb9f474f983355df71f91fd3
Source dataset
uspto-grants-2003_05
Patent number
US06566527B1

Reaction notes

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