Ethanol → HCID 19432769, compound

HRID 1736560Notes

Reaction equation

HRID 1736560 reaction equation
O[C:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C(O[CH2:12][CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16])C.C([OH:21])C>>[OH:21][CH:3]1[CH2:4][CH2:5][CH2:6][CH:2]1[N:7]1[C:17]([NH2:18])=[C:14]([C:15]#[N:16])[C:13]([CH3:12])=[N:8]1

Participants

4

Reactant 3

HCID 702EthanolHCID 45262Malononitrile, (ethoxyethylidene)-HCID 19432831HCID 19432831, compound

Product 1

HCID 19432769HCID 19432769, compoundYield 42%

Procedure

To a stirred solution of 2-(hydroxycyclopentyl)hydrazine (11.6 g, 0.1 mol) in ethanol (75 ml) was added ethoxyethylidene malononitrile (13.6 g, 0.1 mol). The reaction mixture was heated to reflux for 32 hours, cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in boiling isopropanol (100 ml), treated with charcoal and the filtrate was concentrated to approximately 40 ml. The solution was diluted with ether (20 ml), allowed to stand for 1 hour at room temperature and the resulting precipitate was collected by filtration to afford 8.7 g (42%) of 1-(2-hydroxycyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as light orange crystals, m.p. 157°-159° C. when dried at 75° C. in high vacuum.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 32 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved
  5. additiontreated with charcoal
  6. concentrationthe filtrate was concentrated to approximately 40 ml
  7. additionThe solution was diluted with ether (20 ml)
  8. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f52e1bdbbb58485eb1d3b1c700bbe566
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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