Malononitrile → HCID 178509191, compound

HRID 2095147Notes

Reaction equation

HRID 2095147 reaction equation
N1C=CC=C(N[N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])C=1.[NH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C(#N)CC#N.O.[NH2:27][NH2:28]>C(O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([NH:14][N:8]=[C:9]2[C:10]([NH2:11])=[N:28][N:27]=[C:12]2[NH2:13])[CH:16]=1

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 100093-AminopyridineHCID 24654Hydrazine hydrate (1:1)HCID 21955014Pyridin-3-ylcarbonohydrazonoyl dicyanide

Product 1

HCID 178509191HCID 178509191, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(pyridin-3-ylhydrazono)-4H-pyrazole-3,5-diamine was prepared using 2-[(pyridin-3-yl)hydrazono]malononitrile (342 mg, 2 mmol), which was derived from 3-aminopyridine (940 mg, 10 mmol)) and malononitrile (858 mg, 13 mmol), and hydrazine hydrate (110 mg, 2.2 mmol) in ethanol. Solids had not formed after heating the reaction at 80° C. for 40 minutes, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to ambient temperature and the solvent was evaporated. The product was obtained after upon re-crystallization from ethanol as a yellow solid (150 mg); 1H NMR (ppm, DMSO-d6): 6.18 (br., s, 4H), 7.20 (dd, 1H), 8.00 (dd, 1H), 8.38 (d, 1H), 8.85 (s, 1H), 10.77 (br., s, 1H).

Workup

  1. customSolids had not formed
  2. temperatureafter heating
  3. customthe reaction at 80° C. for 40 minutes
  4. customthe solvent was evaporated
  5. customThe product was obtained after
  6. customupon re-crystallization from ethanol as a yellow solid (150 mg)

Sources & evidence

ORD record
ord-372d82534608498caf36ec3cc81c0c25
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

Loading…