Hydrazine → 3-Iodobenzohydrazide

HRID 1672780Notes

Reaction equation

HRID 1672780 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:23][NH2:24]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:23][NH2:24])=[O:6]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 120603-Iodobenzoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 6157743-IodobenzohydrazideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Commercially available 3-iodobenzoic acid (7.41 g, 29.9 mmol) was dissolved in THF (121 mL), and the mixture was stirred at room temperature for 45 minutes after adding 1,1′-carbonyldiimidazole (5.33 g, 32.9 mmol). The mixture was further stirred at room temperature for 2 hours after adding hydrazine.monohydrate (5.3 mL, 109 mmol). The mixture was then concentrated under reduced pressure, and recrystallized from methanol and water to give 3-iodobenzohydrazide (6.08 g, 78%).

Workup

  1. stirringThe mixture was further stirred at room temperature for 2 hours
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customrecrystallized from methanol and water

Sources & evidence

ORD record
ord-93b36c5889284f288b1a13a304a99a82
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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