Acetic Acid → 4-Fluoro-3-methylbenzohydrazide

HRID 239181Notes

Reaction equation

HRID 239181 reaction equation
C(O)(=O)C.C(OC([NH:12][NH:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([CH3:22])[CH:16]=1)=O)(C)(C)C>ClCCl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([NH:13][NH2:12])=[O:23])=[CH:16][C:17]=1[CH3:22]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86686514N'-(4-Fluoro-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 632093974-Fluoro-3-methylbenzohydrazideYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mL trifluor acetic acid was added to 13 g N′-(4-fluoro-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl ester in 150 mL dichlormethane. The reaction was stirred for 1 h at RT and the solvent was evaporated. The residue was basicfied with 1 N sodium hydroxide and extracted with saturated sodium chloride solution and tetrahydrofuran. The organic layer was evaporated and the residue crystallized from ethyl acetate to yield 6.8 g of the desired product.

Workup

  1. customthe solvent was evaporated
  2. extractionextracted with saturated sodium chloride solution and tetrahydrofuran
  3. customThe organic layer was evaporated
  4. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fba27b8f0c1c4370a96ed3d7253a19d1
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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