Water → N-hydroxy-3,5-diiodobenzamide

HRID 2278469Notes

Reaction equation

HRID 2278469 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:5](OC)=[O:6].O.[NH2:14][NH2:15].O>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:12])[CH:11]=1)[C:5]([NH:14][NH2:15])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 53435545Methyl 3,5-diiodobenzoate

Product 1

HCID 67511905N-hydroxy-3,5-diiodobenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To Methyl 3,5-diiodobenzoate (5.0 g, 12.89 mmol) in ethanol (70.0 ml) was added hydrazine hydrate (20.0 ml) under stirring. During heating, white solid was appeared. The reaction was kept 50° C. for 1 h. Heating was stopped and then water (100.0 ml) was added. After cooling down to room temperature, the white product solid was collected by filtration. The product was washed with water and dried under vacuum. Final white product was obtained in 4.6 g (92.0%). 1H NMR (400 MHz, DMSO-d6, δ): 9.92 (s, 1H, NH), 8.22 (t, J=1.6 Hz, 1H), 8.12 (d, J=1.6 Hz, 2H), 4.53 (s, 2H, NH2).

Workup

  1. temperatureDuring heating
  2. temperatureHeating
  3. filtrationthe white product solid was collected by filtration
  4. washThe product was washed with water
  5. customdried under vacuum
  6. customFinal white product was obtained in 4.6 g (92.0%)

Sources & evidence

ORD record
ord-4729e8cf3dc04d0390563825d9137a92
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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