Methanol → Methyl 2-chloropyridine-4-carboxylate

HRID 1635516Notes

Reaction equation

HRID 1635516 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][N:14]=1)[C:9]([OH:11])=[O:10].[CH3:15]O.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][N:14]=1)[C:9]([O:11][CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2736842Methyl 2-chloropyridine-4-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of thionyl chloride (15.0 g, 0.127 mol) in 20 mL of toluene was added 2-chloroisonicotinic acid (10.0 g, 0.063 mol) and the reaction was heated at reflux until gas evolution ceased. Then a solution of methanol (7.7 mL, 0.19 mol) in 10 mL of toluene was added at room temperature over 15 min. The reaction mixture was then refluxed for 1 h and then cooled to room temperature. The clear solution was poured into 100 mL of water, basified with 40% NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate filtered. The filtrate was concentrated in vacuo to give 8.2 g (83%) of product as a brown oil which solidified upon standing, mp: 36-37 C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux until gas evolution
  3. temperatureThe reaction mixture was then refluxed for 1 h
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-52333a2d9d064caaa7ad943d2b837947
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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