2-Fluorobenzoyl chloride → HCID 14370937, compound

HRID 655019Notes

Reaction equation

HRID 655019 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:14](=[O:15])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[F:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 14370937HCID 14370937, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred mixture of 80.0 g of 4-fluorophenylhydrazine hydrochloride in 500 ml of dry pyridine, under nitrogen and cooled in an ice bath, was added, dropwise, 85.8 g of 2-fluorobenzoyl chloride. Upon completion of the addition, the ice bath was removed and the reaction mixture stirred at ambient temperature for 16 hours. The reaction mixture was poured into water and a precipitate formed. The precipitate was recrystallized from ethanol-water to give 97.1 g (80%) of 2-fluorobenzoic acid, 2-(4-fluorophenyl)hydrazide.

Workup

  1. temperatureunder nitrogen and cooled in an ice bath
  2. additionwas added
  3. additionUpon completion of the addition
  4. customthe ice bath was removed
  5. additionThe reaction mixture was poured into water
  6. customa precipitate formed
  7. customThe precipitate was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-4ac86735cc9844918a862ad4f9543c3a
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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