Hydrochloric Acid → Methyl 6-chloropyridine-3-carboxylate

HRID 1938144Notes

Reaction equation

HRID 1938144 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1.[CH3:12]O>C(Cl)Cl>[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:12])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 792226-Chloronicotinic acid

Product 1

HCID 254249Methyl 6-chloropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrochloric acid (gas) was bubbled through a solution of 6.11 g (38.8 mmol) of 6-chloronicotinic acid in approximately 350 ml of methanol. The resultant reaction mixture was reacted for approximately two hours at reflux temperature, then cooled to room temperature and concentrated in vacuo to provide a white residue. This residue was redissolved in methylene chloride and the resultant solution was washed with a saturated sodium bicarbonate solution. The organic portion was dried over sodium sulfate, filtered and then reduced to dryness in vacuo to provide 7.28 g of a tan solid. This solid was crystallized from pentane, followed by recrystallization from hexane to provide the desired titled compound.

Workup

  1. customThe resultant reaction mixture
  2. customwas reacted for approximately two hours
  3. temperatureat reflux temperature
  4. concentrationconcentrated in vacuo
  5. customto provide a white residue
  6. washthe resultant solution was washed with a saturated sodium bicarbonate solution
  7. dry with materialThe organic portion was dried over sodium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7865b4c28af24f3da11da4fd293df0df
Source dataset
uspto-grants-1997_12
Patent number
US05693611

Reaction notes

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