Hydrazine → 2-Hydrazinyl-5-nitropyridine

HRID 261271

Reaction equation

HRID 261271 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH2:11][NH2:12]>CO.O>[NH:11]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[NH2:12]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 40319312-Hydrazinyl-5-nitropyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

To a slurry of 47.6 g (0.3 mol) of 2-chloro-5-nitropyridine in a mixture of 400 ml methanol and 60 ml water and cooled to 10° C. was added with cooling below 30° 86 g hydrazine (95 percent) over about 10 minutes. The solids first went into solution, then a greenish-yellow precipitate separated. The mixture was stirred at reflux for 30 minutes. The greenish solid was filtered off and washed with cold methanol. The solid was slurried in 200 ml of cold water, washed and vacuum dried. The yield was 40.1 g (87 percent).

Workup

  1. additionwas added
  2. customa greenish-yellow precipitate separated
  3. temperatureat reflux for 30 minutes
  4. filtrationThe greenish solid was filtered off
  5. washwashed with cold methanol
  6. washwashed
  7. customvacuum dried

Sources & evidence

ORD record
ord-8b02e0cb6f5744d5ad1be18e9dfdc670
Source dataset
uspto-grants-1979_08
Patent number
US04165238

Linked notes

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