2,5-Difluoroaniline → 4-[(2,5-Difluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinone

HRID 2081196Notes

Reaction equation

HRID 2081196 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[O:10]=[C:11]1[CH2:16][C:15](=O)[CH2:14][CH2:13][NH:12]1>C(O)C>[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][C:15]1[CH2:14][CH2:13][NH:12][C:11](=[O:10])[CH:16]=1

Participants

4

Reactant 2

HCID 677752,5-DifluoroanilineHCID 108878632,4-Piperidinedione

Product 1

HCID 157124974-[(2,5-Difluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinoneYield 20.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,5-difluoroaniline (6.45 g) and 2,4-dioxopiperidine (5.66 g) was heated under nitrogen for 6 h. The reaction mixture was then dissolved in ethanol (50 ml), adsorbed onto silica, and purified by FCC eluting with System A (150:8:1) to give the title compound (2.3 g), m.p. 252°-255°.

Workup

  1. temperaturewas heated under nitrogen for 6 h
  2. custompurified by FCC
  3. washeluting with System A (150:8:1)

Sources & evidence

ORD record
ord-771d264da1a64f40ba416289324aebe6
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

Loading…