Hydrochloric Acid → 3-(3-Bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-one

HRID 1860785Notes

Reaction equation

HRID 1860785 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.N1CCCC1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:17][C:18]1=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 986623-Bromo-4-methoxybenzaldehydeHCID 321710Oxindole

Product 1

HCID 28031073-(3-Bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-p-anisaldehyde (1 g, 4.65 mmol), pyrrolidine (1.9 ml, 23.2 mmol) and oxindole (0.62 g, 4.65 mmol) in dimethylformamide (7 ml) was held in a sealed tube at 100° C. for 12 hours. The mixture was cooled to room temperature and poured into 1N hydrochloric acid (100 ml). The precipitate which formed was filtered and washed with water. The precipitate was then dissolved in ethyl acetate (200 ml), the solution washed with brine, dried over magnesium sulfate and then concentrated. The solid obtained was chromatographed (silica, 30-40% ethyl acetate/hexanes) to give 0.63 g (42%) of 3-(3-bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-one as a yellow solid.

Workup

  1. customThe precipitate which formed
  2. filtrationwas filtered
  3. washwashed with water
  4. dissolutionThe precipitate was then dissolved in ethyl acetate (200 ml)
  5. washthe solution washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe solid obtained
  9. customwas chromatographed (silica, 30-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ee36f4337dad4aa7b3b3be49c0347996
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

Loading…