Tetrahydrofuran → Benzaldehyde, 4-amino-, oxime

HRID 1417745Notes

Reaction equation

HRID 1417745 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1)([O-])=O.O1CCCC1.[H][H]>O>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[N:9][OH:10])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 96339p-NitrobenzaldoximeHCID 178418361HCID 178418361, compound

Product 1

HCID 102410Benzaldehyde, 4-amino-, oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.3 g of 4-nitrobenzaldoxime together with 100 ml of tetrahydrofuran are initially introduced into a stirred autoclave. 50 mg of FeCl2.4 H2O and 0.2 g of the catalyst from Example A1 are added to the solution. Hydrogenation is carried out at 120° C. and a hydrogen pressure of 20×105 pascals. When hydrogenation is complete, the mixture is cooled to room temperature, the reactor is rendered inert with nitrogen and the catalyst is filtered off. The solvent is distilled off to give, after chromatographic purification, 3.5 g (51% of theory) of 4-aminobenzaldoxime.

Workup

  1. customis carried out at 120° C.
  2. filtrationthe catalyst is filtered off
  3. distillationThe solvent is distilled off
  4. customto give
  5. customafter chromatographic purification, 3.5 g (51% of theory) of 4-aminobenzaldoxime

Sources & evidence

ORD record
ord-9eb092de73ae4d899d1819ce918f89d7
Source dataset
uspto-grants-1999_03
Patent number
US05877340

Reaction notes

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