Hydrazine hydrate (1:1) → Methyl 4-hydrazinyl-3-nitrobenzoate

HRID 2073229Notes

Reaction equation

HRID 2073229 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]>C(O)C>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([NH:2][NH2:3])=[C:6]([N+:15]([O-:17])=[O:16])[CH:7]=1)=[O:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 13088284Methyl 4-hydrazinyl-3-nitrobenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

80 ml of hydrazine hydrate were poured into the suspension of 172.5 g of methyl 4-chloro-3-nitrobenzoate in 1600 ml of abs. ethanol under stirring, then the reaction mixture was refluxed while stirring for 45 minutes. The starting material dissolved and the product started to precipitate. After cooling down, the product was filtered by suction, washed with abs. ethanol and water successively until it became free from chloride ion. Thus, 4-methoxycarbonyl-2-nitrophenylhydrazine (143.6 g, 85%) was obtained as yellow crystals m.p.: 169°-171° C.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. dissolutionThe starting material dissolved
  3. customto precipitate
  4. temperatureAfter cooling down
  5. filtrationthe product was filtered by suction
  6. washwashed with abs

Sources & evidence

ORD record
ord-972664d61db6433a97c6b3ba196b2c06
Source dataset
uspto-grants-1990_04
Patent number
US04916149

Reaction notes

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