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

HRID 2261247Notes

Reaction equation

HRID 2261247 reaction equation
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.Cl.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][NH2:19]>CCO>[NH2:9][C:8]1[N:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])[N:19]=[CH:4][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 123660385-Amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At RT, 2-(ethoxymethylene)malononitrile (5.77 g, 47.2 mmol) was added in portions to a stirred suspension of 1-(2-chlorophenyl)hydrazine hydrochloride (8.05 g, 45.0 mmol) and TEA (6.58 ml, 47.2 mmol) in absolute EtOH (56 mL). The mixture was heated to reflux for 1 h. The volatile solvents were removed under reduced pressure. The brown reside was dissolved in EtOAc, washed with water followed by saturated NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile as a rusty crystalline solid. MS (ESI, pos.ion) m/z: 219.0 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe volatile solvents were removed under reduced pressure
  4. dissolutionThe brown reside was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7319fc4a052d47338e9434a11088332f
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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