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

HRID 1112245Notes

Reaction equation

HRID 1112245 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-c1e98f797e1244c3b2397add21f29b73
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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