Hydrazine hydrate (1:1) → 3-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

HRID 655230Notes

Reaction equation

HRID 655230 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1.O.[NH2:15][NH2:16]>C(O)C>[CH3:13][N:11]1[CH:12]=[C:8]([C:5]2[N:4]=[N:3][C:2]([NH:15][NH2:16])=[CH:7][CH:6]=2)[CH:9]=[N:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 545956073-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Product 1

HCID 580751723-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazineYield 218.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3-chloro-6-(1-methyl-1H-pyrazole-4-yl)-pyridazine (1.0 g, 4.81 mmol) in ethanol (20 mL) was added hydrazine monohydrate (2.33 mL, 48 mmol). The reaction mixture was stirred at 80° C. for 3.5 h, cooled to room temperature and concentrated in vacuo. The residue was triturated with 1 N aqueous potassium carbonate, filtered, washed with water and dried in vacuo to provide 2 g of the title compound as a beige solid (670 mg, 73% yield): 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.28 (s, 1H) 7.02 (d, 1H), 7.59 (d, 1H), 7.84 (s, 1H), 7.90 (s, 1H), 8.19 (d, 1H); MS (m/z) 191 [M+H+]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with 1 N aqueous potassium carbonate
  4. filtrationfiltered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f1e971d40661414a82cec2ae7d41ab8c
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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