Water → 3-Iodobenzohydrazide

HRID 2278464Notes

Reaction equation

HRID 2278464 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].O.[NH2:13][NH2:14].O>C(O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:13][NH2:14])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 69258Methyl 3-iodobenzoate

Product 1

HCID 6157743-Iodobenzohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To Methyl 3-iodobenzoate (25.0 g, 95.41 mmol) in ethanol (120.0 ml) was added hydrazine hydrate (50.0 ml). The reaction mixture was reflux for 18 hours. Heating was stopped and then water (300.0 ml) was added. After cooling down to room temperature, white solid was appeared. The white product solid was collected by filtration. The product was washed with water and dried under vacuum. Final white pure product was obtained in 23.0 g (92.0%). 1H NMR (400 MHz, DMSO-d6, δ): 9.85 (s, br, 1H, NH), 8.14 (t, J=1.6 Hz, 1H), 7.85 (m, 1H), 7.82 (m, 1H), 7.25 (t, J=8.0 Hz, 1H), 4.50 (s, 2H, NH2). 13C NMR (100 MHz, CDCl3) δ: 168.54, 155.38, 129.54, 126.72, 125.57, 34.90, 31.07.

Workup

  1. temperatureThe reaction mixture was reflux for 18 hours
  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 pure product was obtained in 23.0 g (92.0%)

Sources & evidence

ORD record
ord-8394bdf72c61446e83cd09616fed63a1
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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