Hydrazine → 1,1-Dimethylethyl 6-chloro-3-hydrazinyl-4-pyridazinecarboxylate

HRID 2189462Notes

Reaction equation

HRID 2189462 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:15])=[CH:6][C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH2:16][NH2:17]>CCO>[Cl:15][C:5]1[N:4]=[N:3][C:2]([NH:16][NH2:17])=[C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 13433721HCID 13433721, compound

Product 1

HCID 134337221,1-Dimethylethyl 6-chloro-3-hydrazinyl-4-pyridazinecarboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3,6-dichloropyridazine-4-carboxylate (66A) (3.9 g, 15.6 mmol) in EtOH (20 mL) was added anhydrous hydrazine (2 mL). The reaction mixture was stirred at room temperature for 2 h, and then concentrated under reduced pressure. The crude product was triturated with 80% EtOH in H2O to afford 1.58 g (40%) of the title compound as a yellow solid. HPLC/MS (Method B): retention time=1.77 min, [M+H]+=189.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was triturated with 80% EtOH in H2O

Sources & evidence

ORD record
ord-2d8a883ff6f64bd38fa88f959ef474e7
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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