4-Hydrazinylpyridine hydrochloride → N-[2-(4-Benzyloxyphenyl)ethylidene]-N'-pyridin-4-ylhydrazine hydrochloride monohydrate

HRID 612458

Reaction equation

HRID 612458 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16]OC)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:19].[NH:20]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[NH2:21]>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH2:8].[ClH:19].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=[N:21][NH:20][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 223202584-Hydrazinylpyridine hydrochlorideHCID 538954501-(4-Benzyloxyphenyl)-2-methoxyethylene

Product 1

HCID 70106552N-[2-(4-Benzyloxyphenyl)ethylidene]-N'-pyridin-4-ylhydrazine hydrochloride monohydrateYield 120.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyloxy-4-(2-methoxyvinyl)benzene (16.9 g), 4-hydrazinopyridine hydrochloride (11.3 g) and p-toluenesulfonic acid (0.68 g) in ethanol (200 ml) was heated under reflux for 5 hrs, with stirring. The reaction mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue crystallized to give 15.75 g (63%) of product, mp 203-205° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hrs
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue crystallized

Sources & evidence

ORD record
ord-664c4c0414f4464d83b98a997d99930d
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Linked notes

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