Hydrochloric Acid → HCID 57151150, compound

HRID 1060775Notes

Reaction equation

HRID 1060775 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][C:10]2=O.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=[O:26].N1CCCCC1.Cl>CN(C)C=O.O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13]([C:12](=[C:19]3[C:20]4[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=4)[NH:17][C:18]3=[O:26])[CH2:11][CH:10]2[CH2:2][C:1]([OH:4])=[O:3])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 321710OxindoleHCID 18002662HCID 18002662, compound

Product 1

HCID 57151150HCID 57151150, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 0.66 g 5-methoxyindan-3-one acetic acid, 2.4 g oxindole and 1.0 ml piperidine in 3 ml of dimethylformamide was heated in a sealed tube at 130° C. for 14 hours. Three ml of 6N hydrochloric acid was added to the cooled reaction mixture followed by 3 ml of water. The supernatant was then decanted. The oily residue was heated in 5 ml of ethanol until it dissolved, the solution was then cooled and water was added. After standing overnight, a solid formed which was filtered and washed with ethanol. The solid was slurried in 4 ml of ethyl acetate at 70° C. for 45 minutes, filtered and suctioned dried to give 300 mg of [6-methoxy-3-(2-oxo-1,2-dihydroindol-3-ylidene)-indan-1-yl]-acetic acid.

Workup

  1. customThe supernatant was then decanted
  2. temperatureThe oily residue was heated in 5 ml of ethanol until it
  3. dissolutiondissolved
  4. temperaturethe solution was then cooled
  5. additionwater was added
  6. customa solid formed which
  7. filtrationwas filtered
  8. washwashed with ethanol
  9. waitThe solid was slurried in 4 ml of ethyl acetate at 70° C. for 45 minutes
  10. filtrationfiltered
  11. customsuctioned dried

Sources & evidence

ORD record
ord-73abb46f31cd47b78785c5653e8ae01b
Source dataset
uspto-grants-2003_02
Patent number
US06525072B1

Reaction notes

Loading…