Methanol → Methyl 6-aminonicotinate

HRID 1006008Notes

Reaction equation

HRID 1006008 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-3f48d5c6c93e4be19181e302b959e31d
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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