2-[3-(Dimethylamino)-1-methoxy-2-propenylidene]malononitrile → 2-Amino-4-Methoxynicotinonitrile

HRID 2361739Notes

Reaction equation

HRID 2361739 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[O:6][CH3:7]>[NH4+].[OH-]>[NH2:12][C:11]1[N:2]=[CH:3][CH:4]=[C:5]([O:6][CH3:7])[C:8]=1[C:9]#[N:10]

Participants

3

Reactant 1

HCID 27867762-[3-(Dimethylamino)-1-methoxy-2-propenylidene]malononitrile

Product 1

HCID 27353592-Amino-4-MethoxynicotinonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of D2 (16 g, 90.39 mmol) in NH4OH (100 ml, 30% in water) was heated at reflux for 3 h. After cooling in an ice bath a yellow solid precipitated. The solid was filtered off, washed with cold isopropanol and dried in vacuo to yield compound D3 (10 g, 76%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling in an ice bath a yellow solid
  4. customprecipitated
  5. filtrationThe solid was filtered off
  6. washwashed with cold isopropanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f11576dd0aa34fe0af5637339d558818
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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