Hydrochloric Acid → 3-(3-Methylindan-1-ylidene)-1,3-dihydroindol-2-one

HRID 1060765Notes

Reaction equation

HRID 1060765 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:21].N1CCCCC1.Cl>CN(C)C=O>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:13]2=[O:21])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 2595603-Methyl-indan-1-oneHCID 321710Oxindole

Product 1

HCID 570344053-(3-Methylindan-1-ylidene)-1,3-dihydroindol-2-oneYield 13.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g of 3-methyl-1-indanone, 1.37 g oxindole and 5 ml piperidine in 3 ml of dimethylforamide was heated in a sealed tube at 130° C. overnight to yield a reddish-brown suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 120 mg of 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid.

Workup

  1. customto yield a reddish-brown suspension
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c77a6c46092244b4b3df3a1cf9dbe9b7
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

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