Hydrochloric Acid → 3-(4-Fluorophenyl)-3-oxo-2-(4-pyridinyl)propanenitrile

HRID 2260520Notes

Reaction equation

HRID 2260520 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH:9]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)[C:10]#[N:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 229090125-(4-Fluorophenyl)-4-(pyridin-4-yl)isoxazole

Product 1

HCID 186256553-(4-Fluorophenyl)-3-oxo-2-(4-pyridinyl)propanenitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5-(4-fluorophenyl)-4-(pyridin-4-yl)isoxazole (5.35 g) in 1N sodium hydroxide aqueous solution (50 ml) was stirred for one hour at 60° C. The solution was cooled and adjusted to pH 6 with concentrated hydrochloric acid. The separated solid was collected, washed with water, and dried to give 3-(4-fluorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile (5.27 g).

Workup

  1. temperatureThe solution was cooled
  2. customThe separated solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-916d87c434434d6cbe962aff0a478310
Source dataset
uspto-grants-1995_12
Patent number
US05478827

Reaction notes

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