Cyclopentylhydrazine hydrochloride → HCID 21830924, compound

HRID 487264

Reaction equation

HRID 487264 reaction equation
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].CO[C:14]1([CH2:20][CH:21]=[C:22]([C:25]#[N:26])[C:23]#[N:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH2:15]1>C(O)C>[CH:2]1([N:7]2[C:25]([NH2:26])=[C:22]([C:23]#[N:24])[C:21]([CH2:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 10942334Sodium MethoxideHCID 86747657HCID 86747657, compound

Product 1

HCID 21830924HCID 21830924, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of cyclopentyl hydrazine hydrochloride (1.4 g, 10.2 mmol), sodium methoxide (0.55 g, 10.2 mmol) and ethanol (30 ml) was heated to reflux and then (1-methoxyphenylethylidene)malononitrile (2.0 g, 10.2 mmol) in ethanol (15 ml) was added dropwise over 1 hour. The reaction mixture was refluxed for 6.5 hours and the solvent was removed in vacuo. The residue was partitioned between chloroform and water, the organic layer was separated and the aqueous layer was extracted with chloroform (3×75 ml). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo to afford 0.7 g (26%) of 1-cyclopentyl-3-phenylmethyl-5-amino-1H-pyrazole-4-carbonitrile as white flakes, m.p. 180°-182° C. when recrystallized from ethyl acetate and dried for 18 hours at 90° C. in high vacuum.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was refluxed for 6.5 hours
  4. customthe solvent was removed in vacuo
  5. customThe residue was partitioned between chloroform and water
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform (3×75 ml)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fee0da0cdac4601a8f3a28dd2a52174
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Linked notes

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