Trichloroisocyanuric Acid → Methyl 2-(chloromethyl)pyridine-3-carboxylate

HRID 2375162Notes

Reaction equation

HRID 2375162 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:12]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>ClCCl>[CH3:7][O:6][C:4]([C:3]1[C:2]([CH2:1][Cl:12])=[N:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 7015327Methyl 2-methylnicotinate

Product 1

HCID 19081344Methyl 2-(chloromethyl)pyridine-3-carboxylateYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-methylnicotinate (20.0 g, 0.132 mol) and trichloroisocyanuric acid (46.0 g, 0.198 mol) in dichloromethane (100 mL) was stirred at room temperature overnight. The reaction mixture was then washed with saturated aqueous sodium carbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated in vacuo to provide the title compound as a yellow liquid (11.2 g), which is used as such in the next step.

Workup

  1. washThe reaction mixture was then washed with saturated aqueous sodium carbonate and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-febc0ad6eea844c3bb2484b40d26e2d7
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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