Ethyl formate → Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-

HRID 437499Notes

Reaction equation

HRID 437499 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].[CH:12]([O-])=[O:13].[Na+].C(OCC)=O>C(O)C.C(O)(=O)/C=C/C(O)=O>[CH:12]([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:13]

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 2723810Sodium FormateHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 5008489Hydrazinecarboxaldehyde, 2-(4-nitrophenyl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 444972Fumaric AcidSolvent

Procedure

4-Nitrophenylhydrazine (9.2 g, 0.06 mole), sodium formate (4.08 g, 0.06 mole), and ethyl formate (148 g, 2.00 moles) were mixed in ethanol (40 ml) and fumaric acid (30 ml). The mixture was heated on a steam bath; the volume of the mixture was reduced to approximately 100 ml by continued boiling. The hydrazide product crystallized out of the concentrated reaction mixture upon cooling. The product was filtered off, washed with ethanol, and dried. Yield 10.2 g (94%), m.p. 183°-185° C.

Workup

  1. temperatureThe mixture was heated on a steam bath
  2. customThe hydrazide product crystallized out of the concentrated reaction mixture
  3. temperatureupon cooling
  4. filtrationThe product was filtered off
  5. washwashed with ethanol
  6. customdried

Sources & evidence

ORD record
ord-322c1f8a52784c6eac53463650da8b2b
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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