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

HRID 1804528Notes

Reaction equation

HRID 1804528 reaction equation
[CH:1]1([NH:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].C(O[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C>C(O)C>[NH2:19][C:18]1[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:7]=[CH:14][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 212350CyclopentylhydrazineHCID 10942334Sodium Methoxide

Product 1

HCID 179603715-Amino-1-cyclopentyl-1H-pyrazole-4-carbonitrileYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Alternate Synthesis of 3: Cyclopentylhydrazine hydrochloride1 (1.08 g, 10 mmol) was dissolved in 100 mL anhydrous ethanol. Sodium methoxide (540 mg, 10 mmol) was added in one portion and the reaction mixture was stirred for ten minutes. Ethoxymethylenemalononitrile (Acros, 1.22 g, 10 mmol) was then added in small portions over several minutes. The reaction mixture was heated at 70° C. under argon overnight. The reaction mixture was concentrated and subjected to flash chromatography on silica gel (stepwise elution: dichloromethane followed by 1:1 hexane:ethyl acetate) to afford 600 mg (34%) of compound 3—identical in all respects with the material obtained above.

Workup

  1. customSynthesis of 3
  2. concentrationThe reaction mixture was concentrated
  3. washstepwise elution

Sources & evidence

ORD record
ord-cdc3334afd9d4a5396f405cc8487ca85
Source dataset
uspto-grants-2013_01
Patent number
US08354414B2

Reaction notes

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