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

HRID 1248956Notes

Reaction equation

HRID 1248956 reaction equation
C(#N)C.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=1)([O-:6])=[O:5].[CH:15](O)=[O:16]>>[CH:15]([NH:14][NH:13][C:10]1[CH:9]=[CH:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:12][CH:11]=1)=[O:16]

Participants

4

Reactant 3

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

Product 1

HCID 5008489Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-Yield 91.2%

Procedure

Then, 1-formyl-2-(4-aminophenyl)hydrazide was synthesized according to the process described in Japanese Patent Application (OPI) No. 74729/79. Namely, to 1.6 l of acetonitrile, 459 g of 4-nitrophenylhydrazine was added with stirring, and 322 g of formic acid was then gradually added thereto to obtain a homogeneous solution. After 20 minutes, crystals were deposited. After carried out the reaction at a temperature of 80° C. for further 2 hours, the mixture was cooled and filtered to separate crystals. The crystals were washed with acetonitrile and dried to obtain 495 g of 1-formyl-2-(4-nitrophenyl)hydrazine. Melting Point: 184° to 186° C.

Workup

  1. customto obtain a homogeneous solution
  2. customthe reaction at a temperature of 80° C. for further 2 hours
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. customto separate crystals
  6. washThe crystals were washed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-b1839bb3ad7e497d90750e928cc5accb
Source dataset
uspto-grants-1986_12
Patent number
US04628024

Reaction notes

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