Hydrazine hydrate (1:1) → 4-(4-Chlorophenyl)-2-hydrazinyl-3,4'-bipyridine

HRID 2101316

Reaction equation

HRID 2101316 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:5]=[CH:4][N:3]=1.O.[NH2:22][NH2:23]>N1C=CC=CC=1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:22][NH2:23])[C:7]=2[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 577993632-Chloro-4-(4-chlorophenyl)-3,4'-bipyridine

Product 1

HCID 577994604-(4-Chlorophenyl)-2-hydrazinyl-3,4'-bipyridineYield 78.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of 2-chloro-4-(4-chlorophenyl)-3,4′-bipyridine (1.3 g, 4.3 mmol) in pyridine (5 mL) at room temperature under argon was added hydrazine monohydrate (2.5 mL, 51.5 mmol). The reaction mixture was stirred at reflux under argon for 15 h. After cooling the reaction mixture to room temperature, most of the solvent was removed under reduced pressure. Water (25 mL) was added to the residue while stirring and a precipitate formed. The precipitate was collected by filtration and washed with water (15 mL×2). After drying under reduced pressure at elevated temperature, 1.0 g of the title compound was obtained as a yellow solid. HPLC/MS: retention time=1.68 min, [M+H]+=297.

Workup

  1. temperatureat reflux under argon for 15 h
  2. custommost of the solvent was removed under reduced pressure
  3. additionWater (25 mL) was added to the residue
  4. stirringwhile stirring
  5. customa precipitate formed
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water (15 mL×2)
  8. customAfter drying under reduced pressure at elevated temperature

Sources & evidence

ORD record
ord-9ee2c7577d5a455c859b9b5cbe713725
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Linked notes

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