p-Toluenesulfonic acid → N-[2-(2-fluoro-5-methoxy-phenyl)ethylidene]-N'-pyridin-4-yl-hydrazine hydrochloride

HRID 612469Notes

Reaction equation

HRID 612469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]=[CH:11]OC.[ClH:14].[NH:15]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[NH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[ClH:14].[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH:11]=[N:16][NH:15][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 223202584-Hydrazinylpyridine hydrochlorideHCID 544075901-Fluoro-4-methoxy-2-(2-methoxyvinyl)benzene

Product 1

HCID 70106711N-[2-(2-fluoro-5-methoxy-phenyl)ethylidene]-N'-pyridin-4-yl-hydrazine hydrochlorideYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-fluoro-4-methoxy-2-(2-methoxyvinyl)benzene (20 g) and 4-hydrazinopyridine hydrochloride (17.7 g) in ethanol (300 ml), p-toluene sulfonic acid (3.13 g) was added, with stirring. The reaction mixture was stirred under reflux for 2 hrs, filtered, and the filtrate was concentrated in vacuo. The residue was recrystallized from methanol to yield 13.24 g (41%) of product, mp 219-220° C.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 2 hrs
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-f28f2580b498436ea1bc02c647703aed
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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