Water → HCID 86613843, compound

HRID 2249393Notes

Reaction equation

HRID 2249393 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([I:11])[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16])(=O)C.C(Cl)(=O)C.O>CO>[NH2:4][C:5]1[CH:10]=[C:9]([I:11])[N:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[C:6]=1[Cl:16]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 86613844HCID 86613844, compound

Product 1

HCID 86613843HCID 86613843, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of 4-acetylamino-3-chloro-6-iodopyridine-2-carboxylic acid, methyl ester (5.0 g, 14 mmol) in methanol (25 mL) was added acetyl chloride (1 mL) and the solution heated under reflux for 1 hour. The solution was cooled and water (25 mL) added and the precipitate was collected. Recrystallization from methanol gave 4-amino-3-chloro-6-iodopyridine-2-carboxylic acid, methyl ester (3.5 g, 11 mmol) mp 152-153° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe solution was cooled
  4. customthe precipitate was collected
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-8dbf45017adf4d5485826a09a4f97c34
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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