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

HRID 442205Notes

Reaction equation

HRID 442205 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-a91e5837ae214bbd83be559b5da9a343
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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