Hydrazine → 3-Bromo-4-chlorobenzhydrazide

HRID 1777024Notes

Reaction equation

HRID 1777024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5](OC)=[O:6].[NH2:13][NH2:14]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([NH:13][NH2:14])=[O:6]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22352523Methyl 3-bromo-4-chlorobenzoate

Product 1

HCID 27355413-Bromo-4-chlorobenzhydrazideYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-bromo-4-chlorobenzoate (120 mg, 0.481 mmol) was added to hydrazine (23.12 mg, 0.721 mmol) in methanol (8 mL) and refluxed for 12 h at 70° C. Reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography affording the title compound (30 mg). 1H NMR (400 MHz, CDCl3): δ 8.02 (d, 1H, J=1.6 Hz), 7.60 (dd, 1H, J=2.0 & 8.0 Hz), 7.52 (d, 1H, J=8.0 Hz). ESI-MS: 250.9 [M+H]+.

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. customthe solvent was removed by vacuum
  4. customcompound was purified by column chromatography

Sources & evidence

ORD record
ord-c3f1201e4e2d4a6387b632193e58ef43
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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