Pyridine → Ethyl 2-fluoro-5-nitrocarbanilate

HRID 36795

Reaction equation

HRID 36795 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH2:10].N1C=CC=CC=1>ClCCl>[F:7][C:8]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:9]=1[NH:10][C:2](=[O:3])[O:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 2754990Ethyl 2-fluoro-5-nitrocarbanilateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.7 g (98.9 mmol) of ethyl chloroformate was added dropwise to a mixture of 15.0 g (94.2 mmol) of 2-fluoro-5-nitroaniline, 8.20 g (104 mmol) of pyridine and 150 ml of dichloromethane at a temperature of not higher than 5° C. Thereafter the temperature was raised to room temperature and the reaction was continued for one night. After the dichloromethane layer was separated out by adding water to the reaction mixture, the dichloromethane layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. Thereafter the dichloromethane was distilled off to obtain the crude product (crystals). The crude product was washed with hexane, thereby obtaining 21.1 g of the objective product (yield: 98%) in the form of ocher crystals.

Workup

  1. waitthe reaction was continued for one night
  2. customAfter the dichloromethane layer was separated out
  3. additionby adding water to the reaction mixture
  4. washthe dichloromethane layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter the dichloromethane was distilled off
  7. customto obtain the crude product (crystals)
  8. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-5b7fd3a86e434faab81ec81274d3d4a9
Source dataset
uspto-grants-1995_05
Patent number
US05416236

Linked notes

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