4-Chloroaniline → HCID 68547209, compound

HRID 1931785Notes

Reaction equation

HRID 1931785 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]([CH2:16][CH3:17])[CH2:11][C:12]([O:14][CH3:15])=[O:13]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]([CH2:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 78124-ChloroanilineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 68547209HCID 68547209, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

In a 300 ml-flask were placed 4-chloroaniline (25.0 g, 196 mmol), methyl 3-oxopentanoate (28.1 g, 216 mmol) and toluene (100 ml). To this solution was added p-toluenesulfonic acid monohydrate (0.19 g, 0.98 mmol), and the resulting mixture was heated in a bath kept at 100° C. under a reduced pressure of 23 kPa for 2.5 hours, while removing the water formed by refluxing by using a Dean-Stark trap. The heating was then discontinued, nitrogen leaked in, and the reaction mixture cooled. The solvent was evaporated off by using a rotary evaporator, and the residue was distilled under reduced pressure to give 33.1 g of the title compound. The yield was 70.5%.

Workup

  1. temperaturethe resulting mixture was heated in a bath
  2. customwhile removing the water
  3. customformed
  4. temperatureby refluxing
  5. temperaturecooled
  6. customThe solvent was evaporated off
  7. customa rotary evaporator
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-f3dde19af25a48398e5369c60ac92a5e
Source dataset
uspto-grants-2012_05
Patent number
US08188307B2

Reaction notes

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