Hydrochloric Acid → 3-Chloro-5-nitro-1H-indazole

HRID 1790162Notes

Reaction equation

HRID 1790162 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)([O-:5])=[O:4].[O-][Cl:16].[Na+].Cl>O>[Cl:16][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=2)[NH:11][N:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 215015-NitroindazoleHCID 23665760Sodium Hypochlorite

Product 1

HCID 1785264933-Chloro-5-nitro-1H-indazoleYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of NaOH (5.00 g, 125 mmol) in H2O (150 mL) was added 5-nitroindazole (5.00 g, 30.7 mmol), and the mixture was heated until a red solution formed. The mixture was cooled in an ice-water bath for 15 minutes, NaClO (60.0 mL, 5.25%, 45.0 mmol) was added and the mixture stirred at 0° C. for 5 hour after which the pH was adjusted to 7 with diluted HCl. The mixture was extracted with ethyl acetate, and the combined organic layer washed with H2O and concentrated under reduced pressure. The residue was purified by flash chromatography to provide the title compound (5.5 g, 92%). 1H NMR (300 MHz, DMSO-d6) ppm 7.78 (m, 1H), 8.28 (m, 1H), 8.61 (m, 1H), MS (DCI/NH3) m/Z 197[M+H]+.

Workup

  1. temperaturethe mixture was heated until a red solution
  2. customformed
  3. temperatureThe mixture was cooled in an ice-water bath for 15 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined organic layer washed with H2O
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3186eb8c24f146f1a18c81ee9a18bf8e
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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