Iodine → HCID 178526562, compound

HRID 79351

Reaction equation

HRID 79351 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([O-:3])=[O:2].[OH-].[K+].[I:15]I.S(=O)(O)[O-].[Na+]>CN(C)C=O>[I:15][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[NH:8][N:7]=1

Participants

6

Reactant 4

HCID 807Iodine2×HCID 14797Potassium Hydroxide2×HCID 180574-NitroindazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178526562HCID 178526562, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-nitro-1H-indazole (50.0 g; 306 mmol) in N,N-dimethylformamide (600 mL) was cooled to 5° C. under a nitrogen atmosphere with stirring. Powdered potassium hydroxide (68.8 g; 1226 mmol) was added. A solution of iodine (156 g; 613 mmol) in DMF (200 mL) was added slowly to the reaction mixture over 2 hours maintaining the temperature between 5 and 10° C. The mixture was stirred at 25° C. for 24 hours. Additional iodine (39.0 g; 153.2 mmol) and potassium hydroxide (17.2 g; 306.5 mmol) was added. The mixture was stirred at 25° C. for a further 12 hours. The reaction mixture was added to an aqueous solution of sodium bisulfite (10% solution; 3300 mL) with stirring. The resulting precipitate was collected by filtration and washed with water. The material was dried in a vacuum oven at 40° C. The material was dissolved in methylene chloride/methanol (10:1; 1.5 L) and filtered through Celite® to remove inorganic impurities. Concentration of the solution under vacuum gave 3-iodo-4-nitro-1H-indazole as a yellow solid (75 g).

Workup

  1. temperaturemaintaining the temperature between 5 and 10° C
  2. stirringThe mixture was stirred at 25° C. for 24 hours
  3. stirringThe mixture was stirred at 25° C. for a further 12 hours
  4. stirringwith stirring
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customThe material was dried in a vacuum oven at 40° C
  8. dissolutionThe material was dissolved in methylene chloride/methanol (10:1; 1.5 L)
  9. filtrationfiltered through Celite®
  10. customto remove inorganic impurities

Sources & evidence

ORD record
ord-8fd7602e27f64a30b95606b1836bde8a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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