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

HRID 24386

Reaction equation

HRID 24386 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-2f6452b5e3b34bc7a1273f75962fcc23
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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