Thionyl Chloride → Methyl 3-aminopicolinate

HRID 1179293Notes

Reaction equation

HRID 1179293 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[C:7]([C:12]([OH:14])=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:15]O.S(Cl)(Cl)=O>CO>[NH2:5][C:6]1[C:7]([C:12]([O:14][CH3:15])=[O:13])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 738363-Aminopicolinic acidHCID 21881854HCID 21881854, compound

Product 1

HCID 9898880Methyl 3-aminopicolinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (75 mL) was cooled to 0° C. and treated dropwise with thionylchloride (3.5 mL, 48 mmol). 3-aminopyridine-2-carboxylic acid (0.9 g, 6.52 mmol, prepared as described by Sucharda, Chem. Ber. 1925, 1727) was added and the mixture brought to reflux. Over the next two days, two more MeOH/thionyl chloride mixtures were made and added to the reaction. The reaction was evaporated to dryness, then treated with thionyl chloride (5.7 mL, 78.3 mmole) in 75 mL of MeOH and refluxed for two more days. The reaction was evaporated to dryness and chromatographed on silica eluting with 9:1:1 EtOH/NH4OH(H2O to give methyl 3-aminopyridine-2-carboxylate as a yellow solid.

Workup

  1. temperatureto reflux
  2. additionadded to the reaction
  3. customThe reaction was evaporated to dryness
  4. temperaturerefluxed for two more days
  5. customThe reaction was evaporated to dryness
  6. customchromatographed on silica eluting with 9:1:1 EtOH/NH4OH(H2O

Sources & evidence

ORD record
ord-fb105b52d3e84b73a66190f742cff1c5
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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