Cyanoacetamide → alpha-Cyano-beta-(2-Nitro-4,5-Dimethoxyphenyl)Acrylamide

HRID 2163573

Reaction equation

HRID 2163573 reaction equation
N1CCCCC1.[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[N+:13]([C:16]1[C:21]([CH:22]=O)=[CH:20][C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)([O-:15])=[O:14]>CO>[C:7]([C:9](=[CH:22][C:21]1[CH:20]=[C:19]([O:24][CH3:25])[C:18]([O:26][CH3:27])=[CH:17][C:16]=1[N+:13]([O-:15])=[O:14])[C:10]([NH2:12])=[O:11])#[N:8]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 885056-Nitroveratraldehyde

Product 1

HCID 4145653alpha-Cyano-beta-(2-Nitro-4,5-Dimethoxyphenyl)Acrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperidine (2.1 g., 0.0237mole) and 2-cyanoacetamide (22.0g., 0.263 mole) are added to a slurry of 6-nitroveratraldehyde (50.0 g., 0.237 mole) in methanol (500 ml.). The mixture is heated to reflux for two hours, and then cooled in an ice bath and filtered. The bright yellow filter cake is washed with cold isopropanol (300 ml.) and then air dried. Yield = 60.1 g. (93%); m.p. 265°-266° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for two hours
  3. temperaturecooled in an ice bath
  4. filtrationfiltered
  5. washThe bright yellow filter cake is washed with cold isopropanol (300 ml.)
  6. customair dried

Sources & evidence

ORD record
ord-2e88bbac5f924a2cb8269c8b139714cc
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Linked notes

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