Hydrazine hydrate (1:1) → 4-Ethoxy-2-(methylsulfanyl)aniline

HRID 2375412Notes

Reaction equation

HRID 2375412 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([S:13][CH3:14])[CH:5]=1)[CH3:2].O.NN>CCO.[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([S:13][CH3:14])[CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 450943324-Ethoxy-2-(methylsulfanyl)-1-nitrobenzene

Product 1

HCID 450913174-Ethoxy-2-(methylsulfanyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-ethoxy-2-methylsulfanyl-1-nitro-benzene (1.0 g, 5.4 mmol) in absolute EtOH (25 mL) at rt was added 40 mg of Pd/C (Aldrich, 10 wt. % on active carbon), followed by slow addition of hydrazine hydrate (0.5 mL). The resulting reaction mixture was refluxed at 90° C. for 3 h. It then cooled to rt, filtered through Celite, and then concentrated in vacuo to afford 4-ethoxy-2-methylsulfanyl-phenyl amine as a pale yellow oil: MS (ESI) 184 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureIt then cooled to rt
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e85869067d641b596256e27fb72e044
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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