Nitroethane → HCID 86711817, compound

HRID 623729Notes

Reaction equation

HRID 623729 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].N1CCCCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[C:14](/[N+:11]([O-:13])=[O:12])\[CH3:15])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8082PiperidineHCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 86711817HCID 86711817, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-2-fluorobenzaldehyde (10 g, 63.1 mmol), nitroethane (54.6 mL, 757 mmol) and piperidine (1.869 mL, 18.92 mmol) were dissolved in toluene (150 mL) and refluxed under Dean Stark conditions overnight. The reaction mixture was cooled to room temperature and the solvents were evaporated. The crude product was purified by column chromatography (silica, heptane/EtOAc 98:2) to give the desired product (10.4 g, 76%) as a yellow solid.

Workup

  1. temperaturerefluxed under Dean Stark conditions overnight
  2. customthe solvents were evaporated
  3. customThe crude product was purified by column chromatography (silica, heptane/EtOAc 98:2)

Sources & evidence

ORD record
ord-22da577dca7b4fedb25968237966343a
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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