Ethanol → 2-(5-Nitro-1H-indazol-1-yl)ethan-1-ol

HRID 388938Notes

Reaction equation

HRID 388938 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.[NH2:13][NH2:14].CCN(C(C)C)C(C)C.[CH2:24]([OH:26])[CH3:25]>CCOC(C)=O>[N+:10]([C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[N:14]([CH2:25][CH2:24][OH:26])[N:13]=[CH:4]2)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 9321HydrazineHCID 729332-Chloro-5-nitrobenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 468357442-(5-Nitro-1H-indazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-nitrobenzaldehyde (4 mmol) in ethanol (10 mL) was added aqueous hydrazine (5 mmol), and the resulting solution was heated at reflux for 2 h to complete hydrazone formation. DIEA (10 mmol) was added to the reaction mixture, and the reaction was subjected to microwave irradiation at 150° C. for 8-10 h. After removal of volatiles in vacuo, the residue obtained was dissolved in EtOAc (30 mL), washed with water (20 mL) and brine (20 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield the product, 2-(5-nitroindazol-1-yl)-ethanol.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 2 h
  3. customirradiation at 150° C. for 8-10 h
  4. customAfter removal of volatiles in vacuo
  5. customthe residue obtained
  6. washwashed with water (20 mL) and brine (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-62075bd02a954cec9e89c5d35cc3aca2
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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