2-(Ethoxymethylene)propanedinitrile → HCID 57438648, compound

HRID 1098134Notes

Reaction equation

HRID 1098134 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH3:9])[NH2:2].C(O[CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16])C>CO>[NH2:18][C:17]1[N:1]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH3:9])[N:2]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 28063924HCID 28063924, compound

Product 1

HCID 57438648HCID 57438648, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydrazinyl-3-methylpyridine (CAS no. 114913-51-8) (700 mg, 5.68 mmol) was suspended in MeOH (30 mL) under nitrogen at −5° C. 2-(ethoxymethylene)malononitrile (694 mg, 5.68 mmol) was added portionwise over 2 mins and the mixture stirred at ˜0° C. for 0.5 hours then heated at reflux for 2 hours. The mixture was allowed to cool and was then evaporated under reduced pressure to afford the crude 5-amino-1-(3-methylpyridin-4-yl)pyrazole-4-carbonitrile which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 2.09 (3H, m), 7.07 (1H, d), 7.87 (2H, m), 7.98 (1H, d), 10.22 (1H, s).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. customwas then evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6e33b57d62441c4b7979329aea0554d
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…