Hydrochloric Acid → HCID 178526561, compound

HRID 706555Notes

Reaction equation

HRID 706555 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].[Cl:15][O-].[Na+].Cl>O>[Cl:15][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, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (2.94 g, 73.6 mmol) in 100 mL of water was added 4-nitro-1H-indazole (3.00 g, 18.39 mmol), followed by sodium hypochlorite (33.4 g, 6.15% aqueous solution). This mixture was allowed to stir at ambient temperature overnight. The mixture was acidified to pH 2 with 10% aqueous HCl and extracted with 25% IPA/DCM. The combined organic extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting solids were triturated with ether to give 1.5 g (41%) of the title compound.

Workup

  1. extractionextracted with 25% IPA/DCM
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solids were triturated with ether

Sources & evidence

ORD record
ord-6fb6fc4ae3694dfe81feabcde3612072
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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