Potassium Iodide → 2-Iodo-7-nitronaphthalene

HRID 1270754Notes

Reaction equation

HRID 1270754 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](N)=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].N([O-])=O.[Na+].[I-:19].[I-].[K+]>Cl.O>[I:19][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 30165Iodide IonHCID 154071007-Nitro-2-aminonaphthaleneHCID 23668193Sodium Nitrite

Product 1

HCID 184515142-Iodo-7-nitronaphthalene

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 7-nitro-2-aminonaphthalene (260 mg, 1.38 mmol) in concentrated HCl (10 mL) is cooled to 0° C. Sodium nitrite (105 mg, 1.53 mmol) is added in portions and the reaction is allowed to stir at 0° C. for 30 minutes. A solution of iodide (175 mg, 253.8 mmol) and potassium iodide (459 mg, 2.76 mmol) in water (5 mL) is added dropwise. After stirring at 0° C. for 1 hour, the solid is removed by filtration. The solid is dissolved in EtOAc and washed with sodium metabisulfite solution, water and brine. The organic layer is dried (Na2SO4) and the solvents evaporated to give 2-iodo-7-nitronaphthalene as an orange solid.

Workup

  1. stirringAfter stirring at 0° C. for 1 hour
  2. customthe solid is removed by filtration
  3. dissolutionThe solid is dissolved in EtOAc
  4. washwashed with sodium metabisulfite solution, water and brine
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-8a2d37c772274f1aafc0678e92247c14
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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