Hydrazine hydrate (1:1) → HCID 10427996, compound

HRID 2106810Notes

Reaction equation

HRID 2106810 reaction equation
O=[C:2]([CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)[CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].O.[NH2:28][NH2:29]>C(O)C>[N+:24]([C:20]1[CH:19]=[C:18]([CH:8]2[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:29][N:28]=[C:2]2[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:23]=[CH:22][CH:21]=1)([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10089532HCID 10089532, compound

Product 1

HCID 10427996HCID 10427996, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2,5-dioxo-3-(3-nitrophenyl)-5-phenylpentanoate (1.5 g) and hydrazine monohydrate (0.24 g) in ethanol (30 ml) was refluxed for 5.5 hours. After evaporating the solvent in vacuo, the residue was subjected to a column chromatography on silica gel (100 ml) eluting with a mixture of benzene and ethyl acetate (50:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure to give ethyl 1,4-dihydro-4-(3-nitrophenyl)-6-phenyl-3-pyridazinecarboxylate (0.52 g).

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. customAfter evaporating the solvent in vacuo
  3. washeluting with a mixture of benzene and ethyl acetate (50:1 V/V)
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3f1a2d7236b43fea789532222bdbd10
Source dataset
uspto-grants-1990_06
Patent number
US04931453

Reaction notes

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