Methanol → Methyl 2,6-dichloroisonicotinate

HRID 1632122Notes

Reaction equation

HRID 1632122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:12]O.S(=O)(=O)(O)O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 93237Methyl 2,6-dichloroisonicotinateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 187 g (0.974 mole) of 2,6-dichloroisonicotinic acid, 1650 ml of methanol and 5 ml of concentrated sulfuric acid was heated at reflux for 24 hours. Most of the solvent was removed in vacuo, leaving crude product which was dissolved in 750 ml of methylene chloride and washed with water and 1N sodium hydroxide. The organic layer was dried (Na2SO4) and solvent removed in vacuo affording 174 g (86.7% yield) of methyl 2,6-dichloroisonicotinate, m.p. 79°-81° C.

Workup

  1. temperatureat reflux for 24 hours
  2. customMost of the solvent was removed in vacuo
  3. customleaving crude product which
  4. washwashed with water and 1N sodium hydroxide
  5. dry with materialThe organic layer was dried (Na2SO4) and solvent
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-cd2d3f54af8f4749935de8c1432f0e67
Source dataset
uspto-grants-1984_10
Patent number
US04474602

Reaction notes

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