Hydroxyamine hydrochloride → 3-Phenyl-1H-5-indazolecarbonitrile

HRID 1649078Notes

Reaction equation

HRID 1649078 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.Cl.[NH2:19]O.C([O-])=O.[Na+]>C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:19]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723810Sodium FormateHCID 130669553-Phenyl-1H-indazole-5-carbaldehyde

Product 1

HCID 130669563-Phenyl-1H-5-indazolecarbonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 22 g of 5-formyl-3-phenylindazole, 8 g of hydroxylamine hydrochloride and 12.5 g of sodium formate was added to 150 ml of formic acid, and after refluxing for 2 hours, the mixture was extracted with chloroform. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to give 16.5 g of 5-cyano-3-phenylindazole (m.p. 150°-151° C.).

Workup

  1. temperatureafter refluxing for 2 hours
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ddde8d3f43fc41eea8b0eccd7d00c7dc
Source dataset
uspto-grants-1983_11
Patent number
US04415569

Reaction notes

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