Hydrochloric Acid → 6-Amino-5-iodonicotinic acid

HRID 1099651Notes

Reaction equation

HRID 1099651 reaction equation
[NH2:1][C:2]1[C:11]([I:12])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[K+].C1COCC1.Cl>CO.O>[NH2:1][C:2]1[C:11]([I:12])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylate

Product 1

HCID 114255416-Amino-5-iodonicotinic acidYield 65%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of methyl 6-amino-5-iodonicotinate (723 mg, 2.6 mmol) and potassium hydroxide (729 mg, 13.0 mmol) in 40 mL methanol/H2O (3:1 ratio) was heated at 50° C. After 4 hours 10 mL THF was added and the reaction continued until 22 hours. The reaction was cooled to room temperature and concentrated HCl added until the solution was pH 4. The solution was concentrated to a volume of 15 mL and the resulting precipitate filtered, rinsed with H2O and 40% EtOAc/hexane to give the title compound as a white solid (443 mg, 65%).

Workup

  1. concentrationThe solution was concentrated to a volume of 15 mL
  2. filtrationthe resulting precipitate filtered
  3. washrinsed with H2O and 40% EtOAc/hexane

Sources & evidence

ORD record
ord-35fde40333234688ae43474f57981766
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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