Pyridine → HCID 13533711, compound

HRID 465126Notes

Reaction equation

HRID 465126 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14]N.[N:16]1C=CC=[CH:18][CH:17]=1>>[CH3:18][C:17]1[N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:2]2=[N:14][N:16]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 9321HydrazineHCID 1329872693297-77-9

Product 1

HCID 13533711HCID 13533711, compound

Procedure

A mixture of 0.5 g of 2'-chloro-2,3'-bipyridine, 5 ml of anhydrous hydrazine and 50 ml of dry pyridine was refluxed for 24 hours, then concentrated under vacuum and the residue dissolved in methylene chloride. The solution was dried and passed through a short pad of hydrous magnesium silicate. The filtrate was concentrated under vacuum to a gum which is 2'-hydrazino-2,3'-bipyridine. To this gum was added 50 ml of triethyl orthoacetate, the mixture was heated on a steam bath for 2.5 hours and concentrated under vacuum. The residue was dissolved in methylene chloride and while boiling, hexane was added. Cooling gave crystals which were recrystallized from methylene chloride-hexane, giving the desired product, mp 142°-143° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationconcentrated under vacuum
  3. dissolutionthe residue dissolved in methylene chloride
  4. customThe solution was dried
  5. concentrationThe filtrate was concentrated under vacuum to a gum which
  6. additionTo this gum was added 50 ml of triethyl orthoacetate
  7. temperaturethe mixture was heated on a steam bath for 2.5 hours
  8. concentrationconcentrated under vacuum
  9. dissolutionThe residue was dissolved in methylene chloride
  10. additionhexane was added
  11. temperatureCooling
  12. customgave crystals which
  13. customwere recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-e6682b8331f340ab84a09b692e0dd5b0
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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