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

HRID 352724Notes

Reaction equation

HRID 352724 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-be3c18d48ea9408a966e3b80f6cf67a4
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…