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

HRID 2081194Notes

Reaction equation

HRID 2081194 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Br:9])[C:3]=1[NH2:4].[O:10]=[C:11]1[CH2:16][C:15](=O)[CH2:14][CH2:13][NH:12]1>>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Br:9])[C:3]=1[NH:4][C:15]1[CH2:14][CH2:13][NH:12][C:11](=[O:10])[CH:16]=1

Participants

3

Reactant 2

HCID 690982,6-DibromoanilineHCID 108878632,4-Piperidinedione

Product 1

HCID 157124964-[(2,6-Dibromophenyl)amino]-5,6-dihydro-2(1H)-pyridinoneYield 29.7%

Procedure

A mixture of 2,6-dibromoaniline (4.4 g) and 2,4-dioxopiperidine (2.0 g) was heated at 120° for 2.5 h. The mixture was then cooled (0°) and triturated with ether 9100 ml) to give a solid which was purified by FCC eluting with System A (100:8:1) to give the title compound (1.8 g), m.p. 240°-243°.

Workup

  1. temperaturewas heated at 120° for 2.5 h
  2. temperatureThe mixture was then cooled (0°)
  3. customtriturated with ether 9100 ml)
  4. customto give a solid which
  5. customwas purified by FCC
  6. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-ac2dbf2e68924409a88120ab5a14fdc4
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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