Potassium Carbonate → Methyl 6-(chloromethyl)pyridine-2-carboxylate

HRID 876550

Reaction equation

HRID 876550 reaction equation
O=S(Cl)[Cl:3].O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Product 1

HCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylateYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

SOCl2 (57 g, 0.48 mol) was added to a solution of methyl 6-(hydroxymethyl)picolinate 70 (40.0 g, 0.239 mol) (Chem. Eur. J. 2006, 12, 6393-6402) in dichloromethane (500 mL) at room temperature. The mixture was stirred at 40° C. for 1 h and sat. aq K2CO3 was added to adjust the pH to 9. The mixture was extracted with CH2Cl2 and the combined organics were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 71 (45 g).

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e824456de4934b2790428962505f9a09
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Linked notes

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