Sodium Hydroxide → 4-(2-Fluoro-4-methoxyphenyl)pyridin-2(1H)-one

HRID 1020692Notes

Reaction equation

HRID 1020692 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([O:16]C)[CH:11]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57950436HCID 57950436, compound

Product 1

HCID 532178004-(2-Fluoro-4-methoxyphenyl)pyridin-2(1H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(2-Fluoro-4-methoxyphenyl)-2-methoxypyridine (1.34 g, 5.72 mmol) was stirred in concentrated hydrochloric acid (25.5 mL) at reflux for 18 h. The reaction was cooled to 0° C. and neutralized with solid NaOH. The resulting solids were collected by filtration and dried under vacuum to yield the title compound (1.09 g, 87%) as a light brown solid: 1H NMR (300 MHz, DMSO-d6) δ 7.52-7.38 (m, 2H), 6.97-6.85 (m, 2H), 6.42-6.33 (m, 2H), 3.80 (s, 3H); ESI MS m/z 220 [M+H]+.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationThe resulting solids were collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-40eab8dd1d18447980e072e53fdeacf7
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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