Water → 1-[(2-Chlorophenyl)amino]acetone

HRID 254331Notes

Reaction equation

HRID 254331 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].I[CH2:10][C:11](=[O:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH2:10][C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 72402-ChloroanilineHCID 11430Potassium CarbonateHCID 763962-Propanone, 1-iodo-

Product 1

HCID 220385051-[(2-Chlorophenyl)amino]acetoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloroaniline (13.2 ml, 0.125 mol), iodoacetone (26.6 g, 0.145 mol) and potassium carbonate (18.1 g, 0.13 mol) in DMF (200 ml) was heated under nitrogen at 100° C. overnight. After cooling to rt, water was added and the mixture extracted with ether (×3). The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated. Flash chromatography (Heptane:EtOAc 80:20) afforded 16.0 g (70%) of the title compound as a brown liquid.

Workup

  1. temperatureAfter cooling to rt
  2. extractionthe mixture extracted with ether (×3)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03e0934f750c47a5a0a14fc09f956b80
Source dataset
uspto-grants-2011_01
Patent number
US07875626B2

Reaction notes

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