Methanol → Methyl 2-chloropyridine-4-carboxylate

HRID 1971272Notes

Reaction equation

HRID 1971272 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:15]O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([O:7][CH3:15])=[O:6])[CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2736842Methyl 2-chloropyridine-4-carboxylateYield 91%

Conditions

Temperature
70 °C

Procedure

2-Chloro-isonicotinic acid (5.10 g, 32.38 mmol) was dissolved in methanol (150 mL). Thionyl chloride (12 mL) was added. This suspension was stirred 5 h at 70° C. and concentrated in vacuo. The residue was dissolved in dichloromethane (250 mL) washed with a solution of 10% aqueous K2CO3 (2×150 mL) dried with MgSO4, filtered and evaporated. Methyl 2-chloropyridine-4-carboxylate SLA 07150 was obtained as a yellow solid (5.06 g, 91%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (250 mL)
  3. washwashed with a solution of 10% aqueous K2CO3 (2×150 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b8fe567b87f54e63b84df13f9a4fb1cb
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

Loading…