Pyridine → 4-Ethyl-2-fluoro-N-(2-hydroxyphenyl)benzamide

HRID 268496Notes

Reaction equation

HRID 268496 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].N1C=CC=CC=1.[CH2:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[C:19]([F:26])[CH:18]=1)[CH3:16]>C1C=CC=CC=1>[CH2:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])=[O:22])=[C:19]([F:26])[CH:18]=1)[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 58012-AminophenolHCID 214138374-Ethyl-2-fluorobenzoyl chloride

Product 1

HCID 214138074-Ethyl-2-fluoro-N-(2-hydroxyphenyl)benzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 13.08 gm. of o-aminophenol in 150 cc. of dry pyridine which is cooled in ice water is added a solution of 4-ethyl-2-fluorobenzoyl chloride (prepared from 20.0 gm. of acid and thionyl chloride) in 30 cc. of dry benzene. The mixture is stirred at room temperature overnight and then concentrated in vacuo. The residue is treated with water and the precipitate collected by filtration to give crude 4-ethyl-2-fluoro-2'-hydroxybenzanilide which was characterized by infra red spectra then used in the following step.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is treated with water
  3. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-a5b5cc4344694a73aff36ec7f2caacf3
Source dataset
uspto-grants-1976_03
Patent number
US03947582

Reaction notes

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