Hydrochloric Acid → 4-Pyridinecarboxylic acid, 2,6-diamino-, methyl ester

HRID 1634207Notes

Reaction equation

HRID 1634207 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[N:10]=1)[C:5]([OH:7])=[O:6].Cl.[CH3:13]O>>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([NH2:11])[N:10]=[C:2]([NH2:1])[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2369872,6-Diaminoisonicotinic acid

Product 1

HCID 111945474-Pyridinecarboxylic acid, 2,6-diamino-, methyl esterYield 77%

Procedure

A suspension of 11 g (70 mmol) 2,6-diamino-isonicotinic acid in 270 ml methanol was treated at 0° C. for 2 h with gaseous HCl. The mixture was concentrated, the residue was dissolved in water and saturated NaHCO3 was added to pH=8. Exhaustive extraction with ethylacetate, drying of the combined organic phases with MgSO4 and removal of the volatiles yielded 9.3 g (77%) 2,6-diamino-isonicotinic acid methyl ester as yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionsaturated NaHCO3 was added to pH=8
  4. extractionExhaustive extraction with ethylacetate
  5. dry with materialdrying of the combined organic phases with MgSO4 and removal of the volatiles

Sources & evidence

ORD record
ord-2861dd4b2cad421b8724947b36d8f6e5
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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