Ethanol → HCID 20228184, compound

HRID 1731657Notes

Reaction equation

HRID 1731657 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][NH2:13])[N:7]=1.[C:14](#[N:18])/[CH:15]=[CH:16]/[CH3:17]>CCOCC>[NH2:18][C:14]1[CH2:15][CH:16]([CH3:17])[N:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([Cl:5])[N:7]=2)[N:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3200042-Chloro-6-hydrazinopyridineHCID 637921CrotononitrileHCID 5360545Sodium

Product 1

HCID 20228184HCID 20228184, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 0.23 g. amount of sodium metal is dissolved in 75 ml. of absolute ethanol, then 7.2 g of 2-chloro-6-hydrazinopyridine is added followed by 3.4 g. of distilled crotononitrile. The reaction mixture is refluxed for 18 hours and the procedure of Example 5 is followed through the anhydrous magnesium silicate filtration step. The filtrate is evaporated to give a dark orange gum which crystallizes on standing. The residue is dissolved in ether, treated with activated charcoal and filtered through diatomaceous earth. The filtrate is concentrated while adding hexane at reflux to yield an oil. The oil is seeded and cooled. Ether is added and continued cooling provides light yellow crystals. The mixture is filtered to give 5.2 g. of the desired product as pale yellow crystals, m.p. 105°-107° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. filtrationthe procedure of Example 5 is followed through the anhydrous magnesium silicate filtration step
  3. customThe filtrate is evaporated
  4. customto give a dark orange gum which
  5. customcrystallizes
  6. dissolutionThe residue is dissolved in ether
  7. additiontreated with activated charcoal
  8. filtrationfiltered through diatomaceous earth
  9. concentrationThe filtrate is concentrated
  10. additionwhile adding hexane
  11. temperatureat reflux
  12. customto yield an oil
  13. temperaturecooled
  14. temperaturecontinued cooling
  15. customprovides light yellow crystals
  16. filtrationThe mixture is filtered
  17. customto give 5.2 g

Sources & evidence

ORD record
ord-0f9c5bb3a9ff40a1bc0ce055652475ae
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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