Methanol → 2-Pyridinecarboxylicacid,5-amino-6-methyl-,methylester(9CI)

HRID 514846Notes

Reaction equation

HRID 514846 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([OH:11])=[O:10])=[N:6][C:7]=1[CH3:8].OS(O)(=O)=O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([O:11][CH3:17])=[O:10])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 82594963HCID 82594963, compound

Product 1

HCID 126402262-Pyridinecarboxylicacid,5-amino-6-methyl-,methylester(9CI)

Conditions

Temperature
60 °C

Procedure

To a solution of 5-amino-6-methylpicolinic acid (31D, 240 mg, 1.5 mmol) in methanol was added conc. H2SO4. The solution was stirred at 60° C. overnight, when LC-MS showed that s.m. was consumed. Then the mixture was concentrated and neutralized with Na2CO3 solution to pH=7. The mixture was extracted with DCM (10 mL×3). The organic layer was dried and concentrated to give the title compound 31E. LC-MS: m/z 167 (M+H)+

Workup

  1. customwas consumed
  2. concentrationThen the mixture was concentrated
  3. extractionThe mixture was extracted with DCM (10 mL×3)
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a781206d0f04361b338bc9bc906ea0e
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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