Water → Methyl 4-(6-aminopyridin-3-yl)benzoate

HRID 1060995Notes

Reaction equation

HRID 1060995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.S(=O)(=O)(O)O.[C:22](=O)(O)[O-].[Na+].O>CO.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([O:14][CH3:22])=[O:13])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 227099024-(6-Aminopyridin-3-yl)benzoic acid

Product 1

HCID 22710768Methyl 4-(6-aminopyridin-3-yl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The resulting 4-(2-aminopyridin-5-yl)benzoic acid (684 mg) was dissolved in methanol (50 ml) at room temperature, followed by the addition of concentrated sulfuric acid (1 ml). After heating under reflux for 2 hours, the reaction mixture was made weakly alkaline with an aqueous solution of sodium bicarbonate. Water and ethyl acetate were added to the resulting mixture to separate the organic layer. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off. Hexane was added to the residue for crystallization, whereby the title compound (243 mg, 23%) was obtained.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 2 hours
  3. customto separate the organic layer
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. additionHexane was added to the residue for crystallization, whereby the title compound (243 mg, 23%)
  7. customwas obtained

Sources & evidence

ORD record
ord-93d1aa63742d4c8089aaa0b0e6e433a6
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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