P-Anisidine → HCID 178492232, compound

HRID 24729Notes

Reaction equation

HRID 24729 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C(N(CC)CC)C.C([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[C:29](Cl)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:21]1=[O:37])(=O)C>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7]/[C:29](=[C:22]2\[C:21](=[O:37])[NH:20][C:28]3[C:23]\2=[CH:24][CH:25]=[CH:26][CH:27]=3)/[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 697436571-Acetyl-3-(1-chloro-1-phenyl-methylidene)-2-indolinone

Product 1

HCID 178492232HCID 178492232, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.18 g (1.5 mmol) of 4-methoxyaniline and 0.2 g (0.28 mmol) of triethylamine are dissolved in 5 ml of dichloromethane and at 5° C. combined with a solution of 0.45 g (1.5 mmol) of 1-acetyl-3-(1-chloro-1-phenyl-methylidene)-2-indolinone in 10 ml of dichloromethane and then stirred for 3 hours at ambient temperature. After removal of the solvent in vacuo the residue is taken up in ethyl acetate/water. The organic phase is washed with water, dried and the solvent is eliminated in vacuo. Then the mixture is dissolved in 15 ml of methanol, combined with 3 ml of 1N sodium hydroxide solution, stirred for 3 hours at ambient temperature and diluted with water and ethyl acetate. The organic phase is dried and concentrated by evaporation. The residue is heated in ethyl acetate, cooled, then suction filtered and dried.

Workup

  1. customAfter removal of the solvent in vacuo the residue
  2. washThe organic phase is washed with water
  3. customdried
  4. dissolutionThen the mixture is dissolved in 15 ml of methanol
  5. stirringstirred for 3 hours at ambient temperature
  6. additiondiluted with water and ethyl acetate
  7. customThe organic phase is dried
  8. concentrationconcentrated by evaporation
  9. temperatureThe residue is heated in ethyl acetate
  10. temperaturecooled
  11. filtrationsuction filtered
  12. customdried

Sources & evidence

ORD record
ord-1b37d1a554874b21b6de10e259d2d9a6
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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