Formic Acid → Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-

HRID 2285584Notes

Reaction equation

HRID 2285584 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(#N)C.[CH:15](O)=[O:16]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][NH:11][CH:15]=[O:16])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 6342AcetonitrileHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 5008489Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-Yield 90.8%

Procedure

459 g of 4-nitrophenylhydrazine was gradually added to 1.6 liters of acetonitrile, and then 322 g of formic acid was added to form a homogeneous solution, and, after 20 minutes, crystals formed. After allowing the reaction to proceed for 2 hours at a temperature of 80° C., the reaction system was cooled and the crystals formed were recovered by filtration, washed with acetonitrile, and dried, to provide 493 g of 2-(4-nitrophenyl)-1-formylhydrazine. Melting point: 184° to 186° C.

Workup

  1. customto form a homogeneous solution
  2. customcrystals formed
  3. customthe reaction
  4. waitto proceed for 2 hours at a temperature of 80° C.
  5. temperaturethe reaction system was cooled
  6. customthe crystals formed
  7. filtrationwere recovered by filtration
  8. washwashed with acetonitrile
  9. customdried

Sources & evidence

ORD record
ord-25ce15e6b88544c786ef00d346d346ca
Source dataset
uspto-grants-1982_04
Patent number
US04323643

Reaction notes

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