2-(Ethoxymethylene)propanedinitrile → HCID 57438640, compound

HRID 1098111Notes

Reaction equation

HRID 1098111 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(O[CH:13]=[C:14]([C:17]#[N:18])[C:15]#[N:16])C>CO>[NH2:18][C:17]1[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=[CH:13][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 5561003-Chloro-2-hydrazinylpyridine

Product 1

HCID 57438640HCID 57438640, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro-2-hydrazinylpyridine (CAS 22841-92-5) (19.1 g, 133.03 mmol) was suspended in MeOH (200 mL) under nitrogen at −5° C. 2-(ethoxymethylene)malononitrile (CAS 123-06-8) (16.25 g, 133.03 mmol) was added portionwise and the resulting mixture stirred at ˜0° C. for 2 hours. The reaction mixture was heated to reflux for 2 hours then cooled and evaporated to provide 5-amino-1-(3-chloropyridin-2-yl)-1H-pyrazole-4-carbonitrile (29.2 g). 1H NMR (400 MHz, DMSO-d6) δ 6.87 (2H, s), 7.61 (1H, dd), 7.79 (1H, s), 8.21 (1H, dd), 8.55 (1H, dd), m/z (ESI+) (M+H)+=220; HPLC tR=1.17 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethen cooled
  4. customevaporated

Sources & evidence

ORD record
ord-8b9d29c83c7145a094e2c55073132860
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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