Ethanol → 3-Amino-5-nitroindazole

HRID 2171214Notes

Reaction equation

HRID 2171214 reaction equation
[OH2:1].[NH2:2][NH2:3].CCO.Cl[C:8]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=[O:17])=[CH:12][C:9]=1[C:10]#[N:11]>O>[N+:16]([C:13]1[CH:12]=[C:9]2[C:8](=[CH:15][CH:14]=1)[NH:3][N:2]=[C:10]2[NH2:11])([O-:17])=[O:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 31366553-Amino-5-nitroindazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrazine monohydrate (4.87 ml) was added to an EtOH (19 ml) solution containing 2-chloro-5-nitrobenzonitrile (1.83 g), followed by stirring for 0.5 hour under ice cooling. Water was added to the reaction solution, and a solid precipitate was collected by filtration and washed with IPE and ethyl acetate. A red solid of 5-nitro-1H-indazol-3-amine (1.45 g) was thus obtained.

Workup

  1. filtrationa solid precipitate was collected by filtration
  2. washwashed with IPE and ethyl acetate

Sources & evidence

ORD record
ord-3f0b002a6c3141b385f1e9d06340fc43
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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