Ethanol → 2-[3-Amino-5-(p-chlorophenyl)-2-pyrazolin-1-yl]-6-chloropyridine

HRID 1731671Notes

Reaction equation

HRID 1731671 reaction equation
[Na].C(O)C.[NH2:5][C:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[N:12]=2)[N:7]=1.[Cl:18][C:19]1[CH:28]=[CH:27][C:22](C=CC#N)=[CH:21][CH:20]=1>ClCCl>[NH2:5][C:6]1[CH2:10][CH:9]([C:22]2[CH:27]=[CH:28][C:19]([Cl:18])=[CH:20][CH:21]=2)[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[N:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 342433-(4-Chlorophenyl)prop-2-enenitrileHCID 5360545SodiumHCID 130509812-(3-Amino-2-pyrazolin-1-yl)-6-chloropyridine

Product 1

HCID 202281782-[3-Amino-5-(p-chlorophenyl)-2-pyrazolin-1-yl]-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An 0.3 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 7.2 g. of 2-chloro-6-hydrazinopyridine (Example 2) is added, followed by 8.2 g. of 4-chlorocinnamonitrile. The reaction mixture is refluxed for 18 hours, then is evaporated in vacuo to a gum. Water is added to give a solid. The solid is collected and dissolved in dichloromethane, dried over magnesium sulfate and filtered. The filtrate is concentrated while adding hexane to separate yellow crystals on cooling. The product is collected and washed with ether-hexane to give 10.3 g. of tan solid. The solid is dissolved in dichloromethane, filtered through absorbent magnesium silicate, then is concentrated while adding hexane to give the product of the Example as white crystals, m.p. 157°-158°.

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hours
  2. customis evaporated in vacuo to a gum
  3. additionWater is added
  4. customto give a solid
  5. customThe solid is collected
  6. dissolutiondissolved in dichloromethane
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated
  10. additionwhile adding hexane
  11. customto separate yellow crystals
  12. temperatureon cooling
  13. customThe product is collected
  14. washwashed with ether-hexane
  15. customto give 10.3 g
  16. filtrationfiltered through absorbent magnesium silicate
  17. concentrationis concentrated
  18. additionwhile adding hexane
  19. customto give the product of the Example as white crystals, m.p. 157°-158°

Sources & evidence

ORD record
ord-ef67ac0d3aaa4262a13655bc94cc903d
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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