Acetic Acid → 4-Bromo-3-methylbenzohydrazide

HRID 336369Notes

Reaction equation

HRID 336369 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]([Br:21])=[C:17]([CH3:22])[CH:16]=1)=O)(C)(C)C>ClCCl>[Br: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 86690170N'-(4-bromo-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 39058874-Bromo-3-methylbenzohydrazideYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mL trifluor acetic acid was added to 70 g N′-(4-bromo-3-methyl-benzoyl)-hydrazinecarboxylic acid tert-butyl ester in 1 L dichlormethane. The reaction was stirred 1 h at RT and evaporated. The residue was basicfied with 1N sodiumhydroxide and extracted with saturated sodiumchloride solution and tetrahyrofuran. The organic layer was evaporated and the residue crystallized with ethyl acetate to give 25 g desired product.

Workup

  1. customevaporated
  2. extractionextracted with saturated sodiumchloride solution and tetrahyrofuran
  3. customThe organic layer was evaporated
  4. customthe residue crystallized with ethyl acetate

Sources & evidence

ORD record
ord-125d8aeb8e25486aa41a4b26d6d0b998
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

Loading…