Methanol → Methyl 6-aminonicotinate

HRID 355764Notes

Reaction equation

HRID 355764 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:16])=[O:9])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 184966-Aminonicotinic acid

Product 1

HCID 737487Methyl 6-aminonicotinate

Procedure

A mixture of 2-amino-5-pyridinecarboxylic acid, methanol (900 ml) and concentrated sulphuric acid (80 ml) was heated at reflux for 18 hours, some of the solvent (500 ml) was evaporated, the pH of the residue was adjusted to 8 with potassium carbonate and the residue was extracted with ethyl acetate (3×200 ml). The organic extracts were dried (MgSO4), filtered and evaporated to give methyl 2-amino-5-pyridinecarboxylate (58.18 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customsome of the solvent (500 ml) was evaporated
  4. extractionthe residue was extracted with ethyl acetate (3×200 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9d3b07ab322044e8ba915f7ffe0f6426
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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