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2-Amino-5-chloropyridine → 2-Amino-5-chloro-3-iodopyridine

HRID 490450
Notes
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Reaction equation

HRID 490450 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[I:9]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 661742-Amino-5-chloropyridineHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 110760102-Amino-5-chloro-3-iodopyridineYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6.43 g of 5-chloropyridin-2-ylamine and 12.38 g of N-iodosuccinimide in 300 ml of glacial acetic acid is heated at around 55° C. for 6 hours. After returning to a temperature of approximately 20° C., the mixture is agitated for approximately 18 hours and then concentrated to dryness under reduced pressure (13 kPa). The residue is taken up with 400 ml of water; the pH of the suspension obtained is brought back to approximately 8 by adding a saturated aqueous sodium hydrogen carbonate solution. The precipitate is filter-dried, washed with water, and dried at 40° C. under reduced pressure (13 kPa) for approximately 3 hours. 12.35 g of 5-chloro-3-iodopyridin-2-ylamine are obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customAfter returning to a temperature of approximately 20° C.
  2. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  3. customthe pH of the suspension obtained
  4. customThe precipitate is filter-dried
  5. washwashed with water
  6. customdried at 40° C. under reduced pressure (13 kPa) for approximately 3 hours

Sources & evidence

ORD record
ord-506e8cb1709847888265fbbfa270d949
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528147B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes