Hydrochloric Acid → 3-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

HRID 1961500

Reaction equation

HRID 1961500 reaction equation
[C:1]([C:3]1[C:4]([NH:14]C=C(C#N)C#N)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1)#[N:2].Cl.[O:22]1CCOCC1>>[NH2:14][C:4]1[C:3]([C:1]#[N:2])=[CH:7][N:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]=1.[NH2:14][C:4]1[C:3]([C:1]([NH2:2])=[O:22])=[CH:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 8005203Propanedinitrile, [[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]methylene]-

Product 2

HCID 27742493-Amino-1-phenyl-1H-pyrazole-4-carbonitrileHCID 88319093-amino-1-phenyl-1H-pyrazole-4-carboxamide

Procedure

{[(4-cyano-1-phenyl-1H-pyrazol-3-yl)amino]methylene}malononitrile (1.07 g, 4.11 mmol) was stirred in refluxing dioxane (80 mL)/2 N HCl (80 mL) for 3 days. Room temperature was attained and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave 3-amino-1-phenyl-1H-pyrazole-4-carbonitrile as a beige solid (A) and 3-amino-1-phenyl-1H-pyrazole-4-carboxamide as a brown solid (B).

Workup

  1. customRoom temperature
  2. extractionthe products extracted into EtOAc (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by MPLC (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-005bf0f697e94a12a37f452a8ace5874
Source dataset
uspto-grants-2013_04
Patent number
US08415346B2

Linked notes

Loading…