Methanol → Methyl 6-chloropyridine-3-carboxylate

HRID 481311Notes

Reaction equation

HRID 481311 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11]O>Cl>[CH3:11][O:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1)=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 792226-Chloronicotinic acid

Product 1

HCID 254249Methyl 6-chloropyridine-3-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

To a slurry of 2.0 g of 6-chloro-3-pyridinecarboxylic acid (Aldrich, 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233 USA) in methanol (200 ml) was added two drops of concentrated aqueous hydrochloric acid and the mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated to give 1.5 g (71%) of product as a white solid. mp 90°-92° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-42fee17e30404f45923d473911804288
Source dataset
uspto-grants-1998_08
Patent number
US05789408

Reaction notes

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