3-Chlorobenzaldehyde → Z-6-bromo-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

HRID 1728089Notes

Reaction equation

HRID 1728089 reaction equation
[Br: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.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.N1CCCC1.ClC1C=C2C(/C(=C/C3C=CC=C(Cl)C=3)/C(=O)N2)=CC=1>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:16]/[C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 31268PyrrolidineHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 57507271Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

Product 1

HCID 68615044Z-6-bromo-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To the mixture of 6-bromooxindole (16.2 g, 92 mmol) (Combi-block) and 3-chloro-benzaldehyde (12.9 g, 92 mmol) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) dropwise. The mixture was then heated at 65° C. for 3 h. After cooled to 4° C., the mixture was filtered and resulting precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 16.2 g, 63%).

Workup

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

Sources & evidence

ORD record
ord-e999bd383f824e86b6c398a1ca21186a
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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