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1,1-Dimethylhydrazine monohydrochloride → 1,3-Dimethyl-5-nitro-1h-indazole

HRID 1022182
Notes
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Reaction equation

HRID 1022182 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=O)[CH3:12].Cl.[CH3:15][N:16](C)[NH2:17]>C(O)C>[CH3:15][N:16]1[C:2]2[C:3](=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[C:11]([CH3:12])=[N:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 739511,1-Dimethylhydrazine monohydrochlorideHCID 899961-(2-Chloro-5-nitrophenyl)ethan-1-one

Product 1

HCID 2909341,3-Dimethyl-5-nitro-1h-indazoleYield 627.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(2-chloro-5-nitrophenyl)ethanone (500 mg, 2.5 mmol) in anhydrous ethanol (15 mL) was added 1,1-dimethylhydrazine hydrochloride (3.38 g, 35.0 mmol) under nitrogen protection. The mixture was heated at reflux for 10 h and evaporated under reduced pressure to afford crude 307a (3.0 g), which was used in the next step without further purification. MS-ESI: [M+H]+ 192.2

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-06c5056355b7415d80bf90a341575807
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716274B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes