Potassium Hydroxide → 6-[(Methyloxy)carbonyl]-2-pyridinecarboxylate potassium salt

HRID 662096Notes

Reaction equation

HRID 662096 reaction equation
[N:1]1[C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:11]([O:13][CH3:14])=[O:12].[OH-].[K+:16]>CO>[K+:16].[CH3:14][O:13][C:11]([C:2]1[N:1]=[C:6]([C:7]([O-:9])=[O:8])[CH:5]=[CH:4][CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 79549Dimethyl pyridine-2,6-carboxylate

Product 1

HCID 686324226-[(Methyloxy)carbonyl]-2-pyridinecarboxylate potassium saltYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of dimethyl 2,6-pyridinedicarboxylate (95.22 g, 488 mmol) in a 2 L round-bottom flask under nitrogen in methanol (1,200 mL; ˜12.5 volumes) was added powdered potassium hydroxide (27.4 g, 488 mmol). The mixture was stirred and after 3 min was almost all in solution. After 20 min lab HPLC showed a 33:62 ratio of starting material to product. Solvent was evaporated and the resulting solid was stirred well with 1000 mL ethyl acetate, then filtered under vacuum, then dried at 40° C. under high vacuum to give 84.5 g (79%) of a white solid that lab HPLC showed to be 98.2% pure (ret time 1.41 min). LC-MS m/z 182 (M+H)+, 0.57 min (ret time).

Workup

  1. waitAfter 20 min lab HPLC showed
  2. customSolvent was evaporated
  3. stirringthe resulting solid was stirred well with 1000 mL ethyl acetate
  4. filtrationfiltered under vacuum
  5. customdried at 40° C. under high vacuum

Sources & evidence

ORD record
ord-57ab9b8ca8b44f7bb1610342bd83a0a2
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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