Methanol → Methyl 6-aminonicotinate

HRID 1653717Notes

Reaction equation

HRID 1653717 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(Cl)(Cl)=O.[CH3:15]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 184966-Aminonicotinic acidHCID 24386Thionyl Chloride

Product 1

HCID 737487Methyl 6-aminonicotinateYield 100%

Procedure

6-Aminonicotinic acid (1.06 g, 7.7 mmol) was suspended with stirring in anhydrous methanol (50 ml), and thionyl chloride (0.55 ml, 7.7 mmol) was added dropwise. The suspension was refluxed to a clear solution over 15 hours. The solvent was evaporated in vacuo and the residue taken up in water (20 ml). The solution was raised to pH 9 (sat. Na2CO3), extracted with chloroform, and dried over MgSO4. Evaporation of the chloroform gave 1.23 g (100%) product as white crystals identified by 400 MHz nmr and ir 1694 cm-1.

Workup

  1. temperatureThe suspension was refluxed to a clear solution over 15 hours
  2. customThe solvent was evaporated in vacuo
  3. temperatureThe solution was raised to pH 9 (sat. Na2CO3)
  4. extractionextracted with chloroform
  5. dry with materialdried over MgSO4
  6. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-98a8aa5124a94800898a0f36c7324c1d
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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