2-(Ethoxymethylene)propanedinitrile → 5-Amino-1-cyclopentyl-1H-pyrazole-4-carbonitrile

HRID 2178731Notes

Reaction equation

HRID 2178731 reaction equation
[CH:1]1([NH:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[CH:11]=[C:12]([C:15]#[N:16])[C:13]#[N:14])C>CO>[NH2:16][C:15]1[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:7]=[CH:11][C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 212350Cyclopentylhydrazine

Product 1

HCID 179603715-Amino-1-cyclopentyl-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopentylhydrazine (6.5 g, 64.9 mmol) is slowly added to a solution of ethoxymethylenemalononitrile (7.93 g, 64.9 mmol) in 100 ml of methanol at room temperature under argon, subsequently heated under reflux for 3 h and then stirred at room temperature overnight. The solvent is stripped off in a rotary evaporator and the residue is stirred with diethyl ether. The solid is filtered off with suction, washed with diethyl ether and dried under high vacuum.

Workup

  1. temperaturesubsequently heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent is stripped off in a rotary evaporator
  4. stirringthe residue is stirred with diethyl ether
  5. filtrationThe solid is filtered off with suction
  6. washwashed with diethyl ether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-77bd0dcd664549dea251fa177e419b9a
Source dataset
uspto-grants-2015_06
Patent number
US09067945B2

Reaction notes

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