Hydrochloric Acid → HCID 178526561, compound

HRID 1790157Notes

Reaction equation

HRID 1790157 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)([O-:5])=[O:4].[O-][Cl:16].[Na+].Cl>O>[Cl:16][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[N+:3]([O-:5])=[O:4])[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 180574-NitroindazoleHCID 23665760Sodium Hypochlorite

Product 1

HCID 178526561HCID 178526561, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of NaOH (0.500 g, 12.5 mmol) in H2O (15.0 mL) was added 4-nitroindazole (0.500 g, 3.07 mmol) after which it was heated until a red solution formed. The solution was immediately placed in an ice-water bath for 15 minutes before NaClO (6.00 mL, 5.25%, 4.50 mmol) was added. The mixture was stirred at 0° C. for 5 hour, the pH adjusted to 7 with dilute HCl and extracted with ethyl acetate. The combined organic layer was washed with H2O, concentrated under reduced pressure and purified by flash chromatography to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.17 (m, 1H), 8.57 (m, 1H), 8.77 (m, 1H), 14.17 (s, 1H); MS (DCI/NH3) m/Z 197[M+H]+.

Workup

  1. temperaturewas heated until a red solution
  2. customformed
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with H2O
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-931258ae9c17455eb502585125c483a9
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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