5-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene → 5-Tert-butyl-3-methanesulphinyl-2-methoxy-phenylamine

HRID 2360509Notes

Reaction equation

HRID 2360509 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]([O:14][CH3:15])=[C:9]([S:11]([CH3:13])=[O:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[C:1]([C:5]1[CH:10]=[C:9]([S:11]([CH3:13])=[O:12])[C:8]([O:14][CH3:15])=[C:7]([NH2:16])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 584939515-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 584939605-Tert-butyl-3-methanesulphinyl-2-methoxy-phenylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

15.5 g 5-tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene in 300 ml of ethyl acetate are added 3.0 g 10% palladium-(II)-hydroxide on charcoal and the mixture is hydrogenated for 16 hours at 3 bar hydrogen pressure. Then the hydrogenation catalyst is filtered off through kieselguhr and washed with 100 ml of ethyl acetate. The solvent is eliminated in vacuo and the residue is extracted from n-pentane.

Workup

  1. filtrationThen the hydrogenation catalyst is filtered off through kieselguhr
  2. washwashed with 100 ml of ethyl acetate
  3. extractionthe residue is extracted from n-pentane

Sources & evidence

ORD record
ord-5d46c9b4eb144564bb6fd2c90b73bd26
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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