Hydrochloric Acid → HCID 71253308, compound

HRID 1029008Notes

Reaction equation

HRID 1029008 reaction equation
S(=O)(=O)(O)O.[N:6]1([C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2N)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1.Cl.N([O-])=O.[Na+].[I-:27].[K+]>O.C(OCC)(=O)C>[I:27][C:16]1[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=1[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 21822801HCID 21822801, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 71253308HCID 71253308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sulfuric acid (7.67 mL, 144 mmol) was added to a solution of 2-(1H-indazol-1-yl)aniline (1.771 g, 8.46 mmol) in concentrated HCl (2.030 mL, 25.4 mmol) at 0° C. The solution was stirred and after cooling back to 0° C., sodium nitrite (0.584 g, 8.46 mmol) in water (3.5 mL) was added dropwise. The reaction was stirred 40 min at 0° C. before potassium iodide (2.81 g, 16.93 mmol) in water (3.5 mL) was added dropwise and the solution was stirred at RT. After 1 h, the reaction is poured into ice with ethyl acetate and separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with 1N HCl, water, saturated sodium bicarbonate, 1N sodium sulfite, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material as an orange oil. The crude material was purified by silica gel chromatography by eluting with 1:4 EtOAc in hexane, to provide 1-(2-iodophenyl)-1H-indazole.

Workup

  1. additionwas added dropwise
  2. stirringthe solution was stirred at RT
  3. customseparated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic extracts were washed with 1N HCl, water, saturated sodium bicarbonate, 1N sodium sulfite
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material as an orange oil
  10. customThe crude material was purified by silica gel chromatography
  11. washby eluting with 1:4 EtOAc in hexane

Sources & evidence

ORD record
ord-3a6afc6d8c28483a9a538e9e67b94274
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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