Methyl acetoacetate → HCID 67253537, compound

HRID 2426971Notes

Reaction equation

HRID 2426971 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6]/[C:13](/[CH3:15])=[CH:12]\[C:11]([O:17][CH3:18])=[O:16])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 2

HCID 7757Methyl acetoacetateHCID 50733624-Chloro-2,6-dimethylaniline

Product 1

HCID 67253537HCID 67253537, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a suspended solution of 4-chloro-2,6-dimethylaniline (24.0 g) in toluene (300 mL) were added methyl acetoacetate (17.9 g) and p-toluenesulfonic acid monohydrate (293 mg) and the mixture was heated to reflux and stirred for 4 hours. The reaction mixture was concentrated. To the obtained residue was added diisopropyl ether and the insoluble matter which was precipitated was removed. The filtrate was concentrated. The obtained residue was purified by preparative medium pressure liquid chromatography W-prep 2XY (column: main column 3L, inject column L; automatic condition setting: hexane:ethyl acetate=9:1, preparative isolation mode GR) to give the title compound (24.7 g) having the following physical data.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. additionTo the obtained residue was added diisopropyl ether
  5. customthe insoluble matter which was precipitated
  6. customwas removed
  7. concentrationThe filtrate was concentrated
  8. customThe obtained residue was purified by preparative medium pressure liquid chromatography W-prep 2XY (column: main column 3L, inject column L; automatic condition setting: hexane:ethyl acetate=9:1, preparative isolation mode GR)

Sources & evidence

ORD record
ord-24e8a484a34a4124803d09cbaf89732f
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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