1,2-Dichloro-4-nitrobenzene → (2-Chloro-4-nitrophenyl)hydrazine

HRID 1709957Notes

Reaction equation

HRID 1709957 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[Cl:14]>C(#N)C>[Cl:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[NH:2][NH2:3]

Participants

4

Reactant 2

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 5029294(2-Chloro-4-nitrophenyl)hydrazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

59 g of hydrazine hydrate was dissolved in 712 ml of acetonitrile at room temperature under an atmosphere of nitrogen. A solution obtained by dissolving 46.3 g of 1,2-dichloro-4-nitrobenzene in 71 g of acetonitrile was added dropwisely to the obtained solution. After the addition had been completed, the obtained mixture was subjected to reflux by heat for 4 hours, and the reaction solution was concentrated. 500 g of water was added to the concentrate, and the produced crystals were filtered off. 200 g of acetonitrile was then added to the crystals, and the obtained mixture was subjected to reflux by heat for 30 minutes and then cooled with ice to room temperature. The produced crystals were filtered off (yield: 27 g).

Workup

  1. customA solution obtained
  2. additionwas added dropwisely to the obtained solution
  3. additionAfter the addition
  4. temperatureto reflux
  5. temperatureby heat for 4 hours
  6. concentrationthe reaction solution was concentrated
  7. addition500 g of water was added to the concentrate
  8. filtrationthe produced crystals were filtered off
  9. addition200 g of acetonitrile was then added to the crystals
  10. temperatureto reflux
  11. temperatureby heat for 30 minutes
  12. filtrationThe produced crystals were filtered off (yield: 27 g)

Sources & evidence

ORD record
ord-000c12f206384d0789810578f08a4c4a
Source dataset
uspto-grants-1990_08
Patent number
US04952483

Reaction notes

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