Methanol → Methyl 6-aminonicotinate

HRID 1019060Notes

Reaction equation

HRID 1019060 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[CH3:11]O>S(=O)(=O)(O)O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:11])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 184966-Aminonicotinic acid

Product 1

HCID 737487Methyl 6-aminonicotinate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6-Aminonicotinic acid (2 g, 22 mmol) was dissolved in methanol (10 ml) and sulphuric acid (0.5 ml). The solution was refluxed over-night and the solvent was evaporated under vacuum. The crude product was dissolved in water-EtOAc and made alkaline by aqueous sodium hydrogencarbonate. Extraction by EtoAc yielded the pure intermediate depicted above (2.3 g, 70%).

Workup

  1. temperatureThe solution was refluxed over-night
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe crude product was dissolved in water-EtOAc
  4. extractionExtraction by EtoAc
  5. customyielded the pure intermediate

Sources & evidence

ORD record
ord-70332cd5f9514c61bf08c1a1dae73430
Source dataset
uspto-grants-2002_11
Patent number
US06486183B1

Reaction notes

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