Cyanoacetamide → alpha-Cyano-beta-(2-Nitro-4-Fluorophenyl)Acrylamide

HRID 2163580Notes

Reaction equation

HRID 2163580 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([CH2:15][C:16]([NH2:18])=[O:17])#[N:14].N1CCCCC1>C(O)C>[C:13]([C:15](=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])[C:16]([NH2:18])=[O:17])#[N:14]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 762264-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 54446537alpha-Cyano-beta-(2-Nitro-4-Fluorophenyl)Acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluoro-2-nitrobenzaldehyde (8.70 g., 51.5 millimoles), 2-cyanoacetamide (4.7 g., 54.4 millimoles), piperidine (0.032 g., 0.37 millimole) and ethanol (80 ml.) is stirred at room temperature for 28 hours. The solid which formed is separated by filtration, washed with ethanol (45 ml.) and dried. Yield = 10 g. (83.5%) of the title acrylamide as light tan crystals M.P. 278°-279° C.

Workup

  1. customThe solid which formed
  2. customis separated by filtration
  3. washwashed with ethanol (45 ml.)
  4. customdried

Sources & evidence

ORD record
ord-d0416a50708741e8b97a95222d2e7f34
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Reaction notes

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