Methanol → Methyl 6-aminonicotinate

HRID 1830525Notes

Reaction equation

HRID 1830525 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 184966-Aminonicotinic acid

Product 1

HCID 737487Methyl 6-aminonicotinateYield 30%

Procedure

A suspension of 6-aminonicotinic acid (2.0 g, 14.5 mmol) and sulfuric acid (2 mL) in methanol (125 mL) was heated at reflux overnight. The solution was cooled, the methanol evaporated and the residue was taken up in water (100 mL) and made basic with NaHCO3 (s), causing a white solid to precipitate. The mixture was extracted with chloroform (3×40 mL) and the combined extracts were dried (MgSO4) and evaporated to afford the ester as an off-white solid (1.04 g, 30%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe solution was cooled
  4. customthe methanol evaporated
  5. customto precipitate
  6. extractionThe mixture was extracted with chloroform (3×40 mL)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-094747e5d4ae4f35bba6ddbe5ddcc6dd
Source dataset
uspto-grants-2006_06
Patent number
US07067516B2

Reaction notes

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