Hydrazine → 2-(Furan-2-yl)aniline

HRID 1294571

Reaction equation

HRID 1294571 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)([O-])=O.NN>C(O)C.[Pd]>[O:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 123772252-(2-Nitrophenyl)furan

Product 1

HCID 46853502-(Furan-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

113 mg (0.6 mmol) 2-(2-nitro-phenyl)-furan are dissolved in 2 ml of ethanol and combined with 6 mg palladium on activated charcoal (10% Pd). 110 μl of a 35% aqueous hydrazine solution are added to this suspension and the reaction mixture is stirred for 20 h under reflux conditions. The catalyst is suction filtered, the filtrate is combined with 25 ml of water and adjusted to pH 5. This mixture is extracted three times with 10 ml of ethyl acetate. The combined organic phases are dried and the solvent is eliminated in vacuo.

Workup

  1. filtrationfiltered
  2. extractionThis mixture is extracted three times with 10 ml of ethyl acetate
  3. customThe combined organic phases are dried

Sources & evidence

ORD record
ord-5c9fa89d29a94b56a8b230fd8def624a
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Linked notes

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