Hydrochloric Acid → 6-Amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylic acid

HRID 489805Notes

Reaction equation

HRID 489805 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([O:12]C)=[O:11])=[CH:4][C:3]=1[I:14].[OH-].[Li+].Cl>CO.O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([OH:12])=[O:11])=[CH:4][C:3]=1[I:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22262635Methyl 6-amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylate

Product 1

HCID 222626676-Amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylic acidYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 6-amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylate (1.4 g, 4.54 mmol) in methanol (30 ml), 1M aqueous lithium hydroxide (9 ml, 9 mmol) was added and the mixture was heated at 70° C. for 2 h. After cooling to room temperature, the mixture was concentrated in vacuo to give a solid. The residual solid was dissolved in water (50 ml) and acidified (pH=5) by addition of 2N aqueous hydrochloric acid. The resultant solid was collected by filtration, washed with water and dried in vacuo under 60° C. to give 1.3 g (92%) of the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customto give a solid
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo under 60° C.

Sources & evidence

ORD record
ord-356adbb358054d1b8c63afb83e93b00f
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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