HCID 22119059, compound → HCID 22119054, compound

HRID 1419116Notes

Reaction equation

HRID 1419116 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([CH3:12])[C:6]([O:13][C:14](=[O:16])[CH3:15])=[C:5]([CH3:17])[C:4]=1[CH3:18].[H][H]>C(O)C.C(OCC)(=O)C.[Pt]=O>[C:14]([O:13][C:6]1[C:5]([CH3:17])=[C:4]([CH3:18])[C:3]([NH:2][CH3:1])=[C:8]([NH2:9])[C:7]=1[CH3:12])(=[O:16])[CH3:15]

Participants

6

Reactant 2

HCID 22119059HCID 22119059, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22119054HCID 22119054, compoundYield 55.7%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.65 g of N-methyl-4-acetoxy-2,3,5-trimethyl-6-nitroaniline (prepared as described in Preparation 18) in a mixture of 20 ml ethanol and 20 ml of ethyl acetate was shaken at room temperature for 3.5 hours and then at 40° C. for 3 hours in an atmosphere of hydrogen and in the presence of 0.2 g of platinum oxide. At the end of this time, the reaction mixture was filtered to remove the platinum oxide and the filtrate was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 1.3 g of title compound, melting at 113°-116° C.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the platinum oxide
  3. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-25b4dbcb32084d808093509907031694
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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