Ammonia → 2-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

HRID 2117729Notes

Reaction equation

HRID 2117729 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:11]([OH:18])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)C#N)=[CH:4][CH:3]=1.N>Br>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69054506HCID 69054506, compound

Product 1

HCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-(4-Fluorophenyl)-3-hydroxy-3-pyridin-4-ylacrylonitrile (0.15 mol/40.6 g) was dissolved in 290 ml of 48% HBr. With vigorous stirring, the reaction mixture was heated under reflux for 24 h. 500 g of ice were then added to the reaction mixture, and the mixture was stirred for another 2 h. After addition of a further 300 g of ice and neutralization of the mixture to pH 7 using concentrated NH3 and a further 60 min of stirring, the title compound was obtained as an ochre-brown precipitate. The precipitate was filtered off, washed with H2O and dried over P2O5 under reduced pressure. Yield: 16.1 g (50%)

Workup

  1. temperatureWith vigorous stirring, the reaction mixture was heated
  2. temperatureunder reflux for 24 h
  3. stirringa further 60 min of stirring

Sources & evidence

ORD record
ord-bb14badee4ce4be08a8bf48856e11562
Source dataset
uspto-grants-2008_10
Patent number
US07442713B2

Reaction notes

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