Iodine → 2-Amino-5-iodo-3-nitropyridine

HRID 1434635

Reaction equation

HRID 1434635 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[I:16]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(O)(=O)C>[I:16][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24477Sodium ThiosulfateHCID 778873-Nitropyridin-2-ylamine

Product 1

HCID 33844682-Amino-5-iodo-3-nitropyridineYield 193.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-3-nitropyridine (5.0 g, 35.9 mmol), acetic acid (22 mL), water (5 mL), sulfuric acid (0.650 mL), and HIO4×2H2O (1.7 g, 7.5 mmol) was allowed to stir at 90° C. for 10 min. Iodine crystals (3.7 g, 14.6 mmol) were added in portions. After stirring for 1 h, the reaction was poured into saturated sodium thiosulfate and extracted with ethyl acetate. The organic layers were washed with 0.1 M NaOH and saturated brine, dried with sodium sulfate, then evaporated to give orange solid (7.5 g, 79% yield).

Workup

  1. stirringAfter stirring for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with 0.1 M NaOH and saturated brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-fffef87291884d818b0849cb29e0c2af
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Linked notes

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