Ethanol → 2-(3-Amino-5-ethyl-2-pyrazolin-1-yl)-6-chloropyridine

HRID 1731660Notes

Reaction equation

HRID 1731660 reaction equation
[Na].[CH2:2](O)[CH3:3].[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.COC(CC)CC#N>O.ClCCl>[NH2:5][C:6]1[CH2:10][CH:9]([CH2:2][CH3:3])[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 5360545SodiumHCID 130509812-(3-Amino-2-pyrazolin-1-yl)-6-chloropyridineHCID 130509853-Methoxypentanenitrile

Product 1

HCID 130509802-(3-Amino-5-ethyl-2-pyrazolin-1-yl)-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

A 0.26 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 8.1 g. of 2-chloro-6-hydrazinopyridine (Example 2) is added followed by 6.4 g. of 3-methoxyvaleronitrile. The reaction mixture is refluxed for 16 hours, then is evaporated in vacuo to give a solid. The solid is dissolved in water/dichloromethane. The organic layer is separated, dried over magnesium sulfate, filtered through anhydrous magnesium silicate and concentrated while adding hexane to yield 7.0 g. of pale yellow crystals. A 200 mg. amount of the crude product is recrystallized from dichloromethanehexane to give 171 mg. of the product of the Example, as pale yellow crystals, m.p. 131°-133° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customis evaporated in vacuo
  3. customto give a solid
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through anhydrous magnesium silicate
  7. concentrationconcentrated
  8. additionwhile adding hexane
  9. customto yield 7.0 g
  10. customamount of the crude product is recrystallized from dichloromethanehexane
  11. customto give 171 mg

Sources & evidence

ORD record
ord-c562b59629534f739b62fa0f41393bb3
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

Loading…