Aniline → 4-Methyl-1-(phenylamino)-pentan-3-one

HRID 74045Notes

Reaction equation

HRID 74045 reaction equation
Cl[CH2:2][CH2:3][C:4](=[O:8])[CH:5]([CH3:7])[CH3:6].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>CC#N>[CH3:6][CH:5]([CH3:7])[C:4](=[O:8])[CH2:3][CH2:2][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 112288301-Chloro-4-methylpentan-3-one

Product 1

HCID 574702544-Methyl-1-(phenylamino)-pentan-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of the crude 1-chloro-4-methylpentan-3-one (about 60 g), aniline (69.8 g, 0.75 mol) and NaHCO3 (210 g, 2.5 mol) in CH3CN (1000 mL) was heated at reflux overnight. After cooling, the insoluble salt was filtered off and the filtrate was concentrated. The residue was diluted with CH2Cl2, washed with 10% HCl solution (100 mL) and brine, dried over Na2SO4, filtered and concentrated to give the crude 4-methyl-1-(phenylamino)-pentan-3-one.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe insoluble salt was filtered off
  5. concentrationthe filtrate was concentrated
  6. additionThe residue was diluted with CH2Cl2
  7. washwashed with 10% HCl solution (100 mL) and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a514cbb5eaf44c3582a39dd7bc676949
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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