Hydrazine hydrate (1:1) → 5-Bromo-2-hydrazinyl-3-methylpyridine

HRID 873992Notes

Reaction equation

HRID 873992 reaction equation
O.[NH2:2][NH2:3].[Br:4][C:5]1[CH:6]=[C:7]([CH3:12])[C:8](Cl)=[N:9][CH:10]=1>COCCO>[Br:4][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([NH:2][NH2:3])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2854345-Bromo-2-chloro-3-methylpyridine

Product 1

HCID 534029825-Bromo-2-hydrazinyl-3-methylpyridineYield 49.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

Hydrazine hydrate (119 mL, 2422 mmol) was added to a suspension of 5-bromo-2-chloro-3-methylpyridine (50 g, 242 mmol) in 2-methoxyethanol (250 mL). The resulting solution was stirred 30 h at 120° C. and concentrated. The yellow residue was purified by trituration with H2O to provide the title compound (24 g) as a colorless solid. tR: 0.39 min (LC-MS 2); ESI-MS: 201.9 [M+H]+ (LC-MS 2)

Workup

  1. concentrationconcentrated
  2. customThe yellow residue was purified by trituration with H2O

Sources & evidence

ORD record
ord-fda35ec996e743919d41ab1c27490192
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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