Hydrazine hydrate (1:1) → 6-Chloro-3-hydrazinylpyridazin-4-amine
Reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[NH2:8].O.[NH2:11][NH2:12]>CCO>[Cl:9][C:5]1[N:4]=[N:3][C:2]([NH:11][NH2:12])=[C:7]([NH2:8])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a stirred suspension of 3,6-dichloropyridazin-4-amine (Step 112.1) (1.49 g, 9.09 mmol) in EtOH (15 mL) was added hydrazine hydrate (11.04 mL, 227 mmol) and the resulting mixture was heated up and stirred at 100° C. for 3 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was triturated with water (25 mL) to afford the title product (478 mg, 3 mmol, 33% yield) as yellow solid. tR: 0.24 min (LC-MS 2); ESI-MS: 160 [M+H]+ (LC-MS 2); ESI-MS: 158 [M−H]− (LC-MS 2).
Workup
- temperaturethe resulting mixture was heated up
- temperatureThe reaction was cooled down to RT
- concentrationconcentrated under reduced pressure
- customThe crude product was triturated with water (25 mL)
Sources & evidence
- ORD record
- ord-fe5ad3ee10bd4892b72eb56e37fdebf1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975417B2
Reaction notes
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