Hydrochloric Acid → 1H-Indazole

HRID 873694Notes

Reaction equation

HRID 873694 reaction equation
S([O-])(=O)(=O)C.Cl.[CH2:7]([NH:14][NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])(=O)C.[Na+]>>[NH:15]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:14]1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 11157(Phenylmethyl)hydrazineHCID 85257MethanesulfonateHCID 517045Sodium Acetate

Product 1

HCID 92211H-Indazole

Procedure

The mesylate (1.0 equivalent) is combined with the HCl salt of the benzyl hydrazine (1.5 equivalent) and sodium acetate (3.0 equivalent) in xylenes (6 vol). The mixture is heated to reflux in a Dean-Stark apparatus until completion. The reaction is cooled to room temperature, poured into 1 N HCl and extracted with toluene. The combined organic extracts are dried over sodium sulfate and concentrated to afford the crude indazole which is purified by flash chromatography.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux in a Dean-Stark apparatus until completion
  3. extractionextracted with toluene
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-054a968c3cc647adab77464cf0e55da3
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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