Water → 4-Iodobenzenecarbohydrazide

HRID 2278458Notes

Reaction equation

HRID 2278458 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][CH:3]=1.O.[NH2:13][NH2:14].O>C(O)C>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:13][NH2:14])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 69273Methyl 4-iodobenzoate

Product 1

HCID 3061044-Iodobenzenecarbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To Methyl 4-iodobenzoate (30.0 g, 114 mmol) in ethanol (180.0 ml) was added hydrazine hydrate (30.0 g, 599 mmol). The reaction mixture was reflux for 22.5 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 26.0 g (86.7%). 1H NMR (400 MHz, DMSO-d6, δ): 9.84 (s, 1H, NH), 7.82 (d, J=8.4 Hz, 2H), 7.59 (d, J=8.4 Hz, 2H), 4.50 (s, 2H, NH2).

Workup

  1. temperatureThe reaction mixture was reflux for 22.5 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 26.0 g (86.7%)

Sources & evidence

ORD record
ord-e3432eedefe34fa6ac649af87649ce34
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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