Hydrochloric Acid → 3-(4-Chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile

HRID 1167562Notes

Reaction equation

HRID 1167562 reaction equation
[Cl: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.[OH-].[Na+].Cl>>[Cl: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 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220374565-(4-Chlorophenyl)-4-(pyridin-4-yl)isoxazole

Product 1

HCID 220374773-(4-Chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrileYield 97.5%

Procedure

A solution of 5-(4-chlorophenyl)-4-(pyridin-4-yl)isoxazole (20.5 g, 79.9 mmol) and 150 mL of a 1N sodium hydroxide solution was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature and adjusted to pH 6 with concentrated hydrochloric acid. The precipitates were filtered, washed with water and ethanol, and dried to give 3-(4-chlorophenyl)-3-oxo-2-(pyridin-4-yl)propanenitrile (20.0 g, quantitative yield). m.p. 225.4-234.9° C. 1H NMR (CDCl3/CD3OD/300 MHz) δ 8.12 (brs, 2H), 7.73-7.59 (m, 5H), 7.30 (d, 3H). ESLRMS m/z 257 (M+H). ESHRMS m/z 257.0481 (M+H, C14H9N20Cl requires 257.0482).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water and ethanol
  3. customdried

Sources & evidence

ORD record
ord-eb743beacc9a46599ad19cd296ddd8dd
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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