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

HRID 1283159Notes

Reaction equation

HRID 1283159 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-3ccbf62b121a4c15bb5352d317a3aab6
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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