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

HRID 1381085Notes

Reaction equation

HRID 1381085 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]>>[CH:15]([NH:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:16]

Participants

4

Reactant 3

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

Product 1

HCID 5008489Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-Yield 91%

Procedure

46 g of 4-nitrophenylhydrazine was added to 160 ml of acetonitrile, and 32.2 g of formic acid was slowly added thereto at a temperature of 60° C. The reaction mixture immediately turned homogeneous and then crystals were again precipitated. The reaction was continued for an additional 2 hours at a temperature of 80° C., followed by cooling. The precipitated crystals were filtered, washed with acetonitrile and dried to obtain 49.5 g of 1-formyl-2-(4-nitrophenyl)hydrazine. Melting Point: 184°-186° C.

Workup

  1. additionwas slowly added
  2. customat a temperature of 60° C
  3. customThe reaction mixture immediately turned homogeneous and then crystals were again precipitated
  4. temperatureby cooling
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-5358f6c313f948e6bc07d1975267157e
Source dataset
uspto-grants-1986_04
Patent number
US04585731

Reaction notes

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