Pentylhydrazine → 1H-Pyrazole-4-carbonitrile, 5-amino-1-pentyl-

HRID 464101Notes

Reaction equation

HRID 464101 reaction equation
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.[CH2:10]([NH:15][NH2:16])[CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[NH2:9][C:8]1[N:15]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[N:16]=[CH:4][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 14247PentylhydrazineHCID 671522-(Ethoxymethylene)propanedinitrile

Product 1

HCID 109210821H-Pyrazole-4-carbonitrile, 5-amino-1-pentyl-Yield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A warm solution of 6.02 g (49.3 mM) ethoxymethylenemalononitrile in 20 ml of ethanol was added via a cannula with stirring to a solution of 6.04 g (59.1 mM) of pentylhydrazine in 20 ml ethanol maintained at 50°. The mixture was then heated to reflux for 30 minutes, then cooled in a refrigerator (ca 3°) for 18 hours. The white crystalline precipitate was filtered to afford 7.73 g (88%) of the title compound; mp, 143°-144°; tlc, Rf =0.50, silica gel, methanol:chloroform (1:19).

Workup

  1. temperaturemaintained at 50°
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 30 minutes
  4. temperaturecooled in a refrigerator (ca 3°) for 18 hours
  5. filtrationThe white crystalline precipitate was filtered

Sources & evidence

ORD record
ord-63c4b0b3c0a848339267d888bb4f0b0f
Source dataset
uspto-grants-1985_10
Patent number
US04546104

Reaction notes

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