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

Reaction equation

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

Participants

Reactant 2

HCID 95842-Fluoroaniline

HCID 108878632,4-Piperidinedione

Product 1

HCID 157124944-[(2-Fluorophenyl)amino]-5,6-dihydro-2(1H)-pyridinoneYield 82.2%

Procedure

A mixture of 2-fluoroaniline (0.98 g) and 2,4-dioxopiperidine (1.0 g) was heated at 120° for 2 h. The cooled mixture was triturated with dry ether (5×40 ml) and the solvent was decanted to leave the title compound (1.495 g), m.p. 98°-100°.

Workup

temperaturewas heated at 120° for 2 h
customThe cooled mixture was triturated with dry ether (5×40 ml)
customthe solvent was decanted

Sources & evidence

ORD record: ord-7ba40ddaf9564399b95a53c6c51609e1
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05183820

Reaction notes

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