Water → 2-Fluorobenzoic acid, 2-(2-fluorophenyl)hydrazide

HRID 359028

Reaction equation

HRID 359028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].[F:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].O>N1C=CC=CC=1.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH:9][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[F:10]

Participants

6

Reactant 3

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 4238442-Fluorophenylhydrazine hydrochloride

Product 1

HCID 151170492-Fluorobenzoic acid, 2-(2-fluorophenyl)hydrazide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution, under nitrogen of 35.2 g of 2-fluorophenylhydrazine in 250 ml of dry pyridine, cooled in an ice bath, was added, dropwise, 36.7 ml of 2-fluorobenzoyl chloride. The reaction mixture was stirred at ambient temperature for 21 hours. Upon dilution of the reaction mixture with water a precipitate was formed. Attempts to separate the precipitate by filtration, washing with pyridine, resulted in the formation of an oil. That portion of oil which did not pass into the filtrate was dissolved in dichloromethane and concentrated in vacuo. Upon standing, the filtrate separated into aqueous and organic phases Treatment of the organic phase with toluene resulted in the formation of a precipitate. Recrystallization of the combined product from toluene yielded 49.2 g of 2-fluorobenzoic acid, 2-(2-fluorophenyl)hydrazide.

Workup

  1. additionwas added
  2. customto separate the precipitate
  3. filtrationby filtration
  4. washwashing with pyridine
  5. customresulted in the formation of an oil
  6. concentrationconcentrated in vacuo
  7. customthe filtrate separated into aqueous and organic phases Treatment of the organic phase with toluene
  8. customresulted in the formation of a precipitate
  9. customRecrystallization of the combined product from toluene

Sources & evidence

ORD record
ord-ce2dccd87b334ae78e518d6c045b68d0
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Linked notes

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