Hydrazine hydrate (1:1) → HCID 18693261, compound

HRID 1870776Notes

Reaction equation

HRID 1870776 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([CH3:29])=[CH2:28])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17](OCCCC)=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].O.[NH2:31][NH2:32]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:26][C:27]([CH3:29])=[CH2:28])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:15][C:14]([C:17]([NH:31][NH2:32])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18693256HCID 18693256, compound

Product 1

HCID 18693261HCID 18693261, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Butyl 6-[N-(5-bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate (reference example 4) (4.3 g, 9.3 mmol) was dissolved in ethanol (170ml) with hydrazine hydrate (17 ml, 330 mmol) and heated at reflux for 16 hours. The solvent was removed in vacuo, and the residue treated with ethyl acetate/water (200 ml of each). The organic phase separated off and the aqueous phase reextracted with ethyl acetate (2×200 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the title compound as an oil which crystallised on standing (3.66 g, 94%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. additionthe residue treated with ethyl acetate/water (200 ml of each)
  5. customThe organic phase separated off
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dac3dff0ad94837988b131e16f0badc
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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