Hydrochloric Acid → HCID 178526490, compound

HRID 1790165Notes

Reaction equation

HRID 1790165 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].[Br-:15].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.Cl>O.CO>[Br:15][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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 215015-NitroindazoleHCID 21124087Pyridiniumtribromide

Product 1

HCID 178526490HCID 178526490, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of NaOH (2.0 g) in H2O (60 mL) was added 5-nitroindazole (2.0 g, 12 mmol), and the mixture was heated until a red solution formed. The mixture was placed in an ice-water bath for 15 minutes after which pyridinium tribromide (4.7 g, 15 mmol) in methanol (15 mL) was added. The mixture was stirred at 0° C. for 5 hours, the pH adjusted to 7 with diluted HCl and the mixture extracted with ethyl acetate. The combined organic layers were washed with H2O, concentrated under reduced pressure and purified by flash chromatography to provide the title compound (1.6 g, 55% yield). 1H NMR (300 MHz, DMSO-d6) ppm 7.80 (m, 1H), 8.28 (m, 1H), 8.50 (m, 1H), 14.09 (s, 1H), MS (DCI/NH3) m/z 243[M+H]+.

Workup

  1. temperaturethe mixture was heated until a red solution
  2. customformed
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe combined organic layers were washed with H2O
  5. concentrationconcentrated under reduced pressure
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cc15a859aa5645abafbaf42d9c833fd3
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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