Hydrazine hydrate (1:1) → 2-Iodo-5-methoxyaniline

HRID 1825167Notes

Reaction equation

HRID 1825167 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.O.NN>CO>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2926594-Iodo-3-nitroanisole

Product 1

HCID 111395082-Iodo-5-methoxyanilineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-iodo-3-nitroanisole (5 g, 17.9 mmole) in 100 ml methanol was added FeCl3 (50 mg, 0.3 mmole) and activated carbon (40 mg). The mixture was heated to reflux and hydrazine hydrate (1.75 g, 35 mmole) was added dropwise. The mixture was refluxed for an additional 8 hours and cooled to room temperature, filtered through Celite. The filtrate was concentrated and purified by column chromatography (eluting with 10% EtOAc in hexanes) to give 4.05 g product as pale yellow oil (91% yield). 1H NMR (300 MHz, CDCl3) δ 7.47 (1H, d, J=8.7 Hz), 6.31 (1H, d, J=2.8 Hz), 6.13 (1H, dd, J=2.8, 8.7 Hz), 3.73 (3H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for an additional 8 hours
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (eluting with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d2a24bd85fe24d4b8f20c23c131c7327
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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