Hydrochloric Acid → 3-(4-Methyl-indan-1-ylidene)-1,3-dihydroindol-2-one

HRID 478706Notes

Reaction equation

HRID 478706 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.[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][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][C:13]1=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 321710OxindoleHCID 44184314-Methyl-1-indanone

Product 1

HCID 570147493-(4-Methyl-indan-1-ylidene)-1,3-dihydroindol-2-oneYield 44.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.5 g 4-methyl-1-indanone, 1.37 g oxindole and 3 ml piperidine in 5 ml dimethylforamide was heated in a sealed tube at 130° C. for 3 days to yield a reddish-black suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine dried over magnesium sulfate and concentrated. The resulting solid was precipitated from ethyl acetate/hexanes (2×) followed by methylene chloride/hexanes to afford 400 mg of 3-(4-methyl-indan-1-ylidene)-1,3-dihydroindol-2-one as a yellow solid.

Workup

  1. customto yield a reddish-black suspension
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting solid was precipitated from ethyl acetate/hexanes (2×)

Sources & evidence

ORD record
ord-12d91fa561b9402c8a7c6dc2da5955c3
Source dataset
uspto-grants-2003_11
Patent number
US06642251B1

Reaction notes

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