Pyrrolidine → Methyl 4-chloro-2-[(6-chloro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]benzoate

HRID 1728222Notes

Reaction equation

HRID 1728222 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[CH:22]=O.N1CCCC1.ClC1C=C2C(/C(=C/C3C=C(Cl)C=CC=3O)/C(=O)N2)=CC=1>CO>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[CH:22]=[C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:11]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 57566138methyl 4-chloro-2-formylbenzoateHCID 86760834HCID 86760834, compound

Product 1

HCID 57566241Methyl 4-chloro-2-[(6-chloro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To the mixture of 6-chlorooxindole (1.2 g, 7 mmol) and 4-chloro-2-formyl-benzoic acid methyl ester (1.4 g, 7 mmol) in methanol (10 mL) was added pyrrolidine (490 mg, 7 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to 4° C., the mixture was filtered and the precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(5-chloro-2-hydroxy-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (500 mg).

Workup

  1. temperatureAfter cooled to 4° C.
  2. filtrationthe mixture was filtered
  3. customthe precipitate was collected
  4. customdried
  5. customto give

Sources & evidence

ORD record
ord-26e00217062d4bec9889aa95da59b997
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…