Methyl Isobutyl Ketone → HCID 19827543, compound

HRID 1494442Notes

Reaction equation

HRID 1494442 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O.[CH3:12][CH:13]([CH3:18])[CH2:14][C:15](=O)[CH3:16]>[Pt].OS(O)(=O)=O.CO>[CH3:16][CH:15]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[CH2:14][CH:13]([CH3:18])[CH3:12]

Participants

6

Reactant 2

HCID 7909Methyl Isobutyl KetoneHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 19827543HCID 19827543, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

159.1 g of 2,4-difluoronitrobenzene and 150 g of 4-methylpentan-2-one are mixed in 1.2 1 of methanol with 3 g of concentrated H2SO4 and 5 g of 5% Pt/C, and the mixture is catalytically hydrogenated for 3 hours at 30°-35° under a constant 5 bar of H2. The progress of the hydrogenation is monitored by thin-layer chromatography on silica gel using the mixture petroleum ether/dioxane 4:1 as the mobile phase. When the reaction is complete, the catalyst is filtered off and the solvent is removed by distillation on a rotary evaporator. A brown oil remains which, after removal of some resinous by-product, is rectified in vacuo. The fraction of boiling point 120°-125° at 14 mbar is collected. 173.4 g of N-(1,3-dimethylbutyl)-2,4-difluoroaniline are obtained as a colourless oil.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solvent is removed by distillation on a rotary evaporator
  3. customA brown oil remains which, after removal of some resinous by-product
  4. customThe fraction of boiling point 120°-125° at 14 mbar is collected

Sources & evidence

ORD record
ord-a88f45d1a65249f38cbdba3da09ebc5f
Source dataset
uspto-grants-1991_06
Patent number
US05026625

Reaction notes

Loading…