Ethanol → 1-(5-chloro-2-pyridinyl)-5-methyl-4,5-dihydro-1H-pyrazol-3-amine

HRID 1731658Notes

Reaction equation

HRID 1731658 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:7]=[N:8][C:9]([NH:12][NH2:13])=[CH:10][CH:11]=1.[C:14](#[N:18])/[CH:15]=[CH:16]/[CH3:17]>ClCCl.CCCCCC>[NH2:18][C:14]1[CH2:15][CH:16]([CH3:17])[N:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][N:8]=2)[N:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 637921CrotononitrileHCID 5360545SodiumHCID 135904645-Chloro-2-hydrazinylpyridine

Product 1

HCID 202281911-(5-chloro-2-pyridinyl)-5-methyl-4,5-dihydro-1H-pyrazol-3-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A mixture of 0.20 g. of sodium metal dissolved in 50 ml. of absolute ethanol, 5.0 g. of 3-chloro-6-hydrazinopyridine and 4.8 g. of crotononitrile is heated at reflux for 18 hours. The procedure of Example 5 is followed through the evaporation of the magnesium silicate filtrate to give a yellow gum. Trituration with hexane gives a yellow solid. The solid is dissolved in dichloromethane. This solution is concentrated by heating on a steam bath while adding hexane, then is cooled in a refrigerator to separate 3.3 g. of the product of the Example as pale yellow crystals, m.p. 168°-170° C.

Workup

  1. additionA mixture of 0.20 g
  2. temperatureat reflux for 18 hours
  3. customThe procedure of Example 5 is followed through the evaporation of the magnesium silicate filtrate
  4. customto give a yellow gum
  5. concentrationThis solution is concentrated
  6. temperatureby heating on a steam bath
  7. additionwhile adding hexane
  8. temperatureis cooled in a refrigerator
  9. customto separate 3.3 g

Sources & evidence

ORD record
ord-4aa3884e17434c45b55fe507fe3d221a
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

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