Sodium Azide → Methyl 4-aminopyridine-2-carboxylate

HRID 1252994Notes

Reaction equation

HRID 1252994 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.[N-:12]=[N+]=[N-].[Na+]>CN(C)C=O>[NH2:12][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 3759117Methyl 4-aminopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g of methyl 4-chloropicolinate and 2 g of sodium azide in 20 ml of dimethylformamide is stirred at 100° for 8 hours. The solvent is removed in vacuo, the reaction is diluted with water and the product extracted into ethyl acetate. After drying over magnesium sulfate, the solvent is removed in vacuo. The residue is hydrogenated in 30 ml of ethanol at atmospheric pressure over 500 mg of 10% palladium on carbon catalyst for 3 hours. After filtration through filter-cel the solvent is removed in vacuo and the residue crystallized from ether to afford methyl 4-aminopicolinate.

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe reaction is diluted with water
  3. extractionthe product extracted into ethyl acetate
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent is removed in vacuo
  6. waitThe residue is hydrogenated in 30 ml of ethanol at atmospheric pressure over 500 mg of 10% palladium on carbon catalyst for 3 hours
  7. filtrationAfter filtration
  8. filtrationthrough filter-cel the solvent
  9. customis removed in vacuo
  10. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-68ec20ca6a7748efb1880c0ca890593a
Source dataset
uspto-grants-1988_05
Patent number
US04746653

Reaction notes

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