2-Fluorobenzoyl chloride → 2-Fluorobenzoic acid, 2-(4-(trifluoromethyl)phenyl)hydrazide

HRID 359020

Reaction equation

HRID 359020 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17]>N1C=CC=CC=1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH:10][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[F:13])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 1362004-(Trifluoromethyl)phenylhydrazine

Product 1

HCID 151170472-Fluorobenzoic acid, 2-(4-(trifluoromethyl)phenyl)hydrazideYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 75.0 g of 4-(trifluoromethyl)-phenylhydrazine in 500 ml of dry pyridine, cooled in an ice bath, was added dropwise, under nitrogen, 79.1 g of 2-fluorobenzoyl chloride. Upon completion of the addition, the ice bath was removed and the reaction mixture stirred at ambient temperature for 4 hours. The mixture was poured into water and a precipitate formed. Recrystallization of the precipitate from isopropyl alcohol-water, gave 108 g (84%) of 2-fluorobenzoic acid, 2-(4-(trifluoromethyl)phenyl)hydrazide as a solid. Subsequent recrystallization from isopropyl alcohol-water gave the analytical sample, mp 163°-165°.

Workup

  1. additionwas added dropwise, under nitrogen
  2. additionUpon completion of the addition
  3. customthe ice bath was removed
  4. additionThe mixture was poured into water
  5. customa precipitate formed
  6. customRecrystallization of the precipitate from isopropyl alcohol-water

Sources & evidence

ORD record
ord-84092de639474d16a10f7b220f423f39
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Linked notes

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