Methanol → Methyl 3-aminopyridine-4-carboxylate

HRID 1640970Notes

Reaction equation

HRID 1640970 reaction equation
[NH2:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 1488824Methyl 3-aminopyridine-4-carboxylate

Procedure

A mixture of 3-amino-isonicotinic acid (613 mg, 4.44 mmol), methanol (15 mL) and thionyl chloride (0.7 mL, 8.88 mmol) was stirred at reflux for 3 days. The volatiles were removed under reduced pressure and the residue stirred with diethylether (20 mL) and saturated solution of sodium hydrogenocarbonate (40 mL). The phases were separated and the aqueous phase extracted with diethylether (2×20 mL). The combined organic phases were dried over sodium sulfate and evaporated to dryness affording 400 mg of the title compound.

Workup

  1. temperatureat reflux for 3 days
  2. customThe volatiles were removed under reduced pressure
  3. stirringthe residue stirred with diethylether (20 mL) and saturated solution of sodium hydrogenocarbonate (40 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase extracted with diethylether (2×20 mL)
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9a882ae3105b4033ad451eb4d7b0019e
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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