Hydrazine → 5-Bromo-4-(4-chlorophenyl)-2-hydrazinylpyridine

HRID 2266328Notes

Reaction equation

HRID 2266328 reaction equation
[Br:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[NH2:16][NH2:17]>C1COCC1>[Br:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][C:5]([NH:16][NH2:17])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 579797375-Bromo-2-chloro-4-(4-chlorophenyl)pyridine

Product 1

HCID 579797505-Bromo-4-(4-chlorophenyl)-2-hydrazinylpyridineYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-bromo-2-chloro-4-(4-chlorophenyl)pyridine (1.3 g, 4.3 mmol) in THF (10 mL) was added hydrazine (1.4 g, 43 mmol). The reaction mixture was refluxed under argon for 4 days, then allowed to cool to 20° C. and concentrated in vacuo. The residue was purified by using reverse phase preparative HPLC (Conditions: Phenomenex Luna 5μ C18 30×100 mm; Eluted with 0% to 100% B, 10 min gradient, 100% B hold for 5 min, (A=90% H2O, 10% CH3CN, 0.1% trifluoroacetic acid and B=10% H2O, 90% CH3CN, 0.1% trifluoroacetic acid); Flow rate at 40 mL/min, UV detection at 220 nm), followed by basification with 1N aqueous NaOH to pH 12 and extraction with CHCl3 to afford 0.82 g (63%) of the title compound as an off-white solid. LC/MS (method B): retention time=1.47 min, [M+H]+=298.0.

Workup

  1. temperatureThe reaction mixture was refluxed under argon for 4 days
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified
  4. washEluted with 0% to 100% B, 10 min gradient, 100% B hold for 5 min
  5. extractionFlow rate at 40 mL/min, UV detection at 220 nm), followed by basification with 1N aqueous NaOH to pH 12 and extraction with CHCl3

Sources & evidence

ORD record
ord-a1cddf0088f040cb8a80a9bddd59e445
Source dataset
uspto-grants-2010_12
Patent number
US07858639B2

Reaction notes

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