Acetic Acid → 3-(6-Chloro-1-oxo-2,3-dihydro-1H-inden-2-yl)propanoic acid

HRID 326007Notes

Reaction equation

HRID 326007 reaction equation
N1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=3)[CH2:8][CH:7]=2)CCCC1.[C:16]([O:20]C)(=[O:19])[CH:17]=[CH2:18].C(O)(=[O:24])C.Cl>O1CCOCC1>[Cl:15][C:12]1[CH:13]=[C:14]2[C:9]([CH2:8][CH:7]([CH2:18][CH2:17][C:16]([OH:20])=[O:19])[C:6]2=[O:24])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 204636741-(5-Chloro-1H-inden-3-yl)pyrrolidine

Product 1

HCID 130516493-(6-Chloro-1-oxo-2,3-dihydro-1H-inden-2-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Twenty-two (22) grams of 3-pyrrolidino-5-chloroindene and 18 g of methyl acrylate were dissolved in 70 ml of dioxane, refluxed for 5 hours and freed of the solvent by distilling it off, to obtain a residue. The thus obtained residue was incorporated with 100 ml of acetic acid and 100 ml of hydrochloric acid and heated for 3 hours. After the end of the reaction, the resulting reaction mixture was freed of the solvent by distilling it off under a reduced pressure and incorporated with iced water to precipitate crystals. The crystals so precipitated were filtered off, washed with water, dried and then recrystallized from ethyl acetate to obtain 16 g of 6-chloro-1-oxo-2,3-dihydro-2-indene propionic acid in the colorless needle form.

Workup

  1. temperaturerefluxed for 5 hours
  2. distillationby distilling it off,
  3. customto obtain a residue
  4. temperatureheated for 3 hours
  5. customAfter the end of the reaction
  6. customthe resulting reaction mixture
  7. distillationby distilling it off under a reduced pressure
  8. customincorporated with iced water to precipitate crystals
  9. customThe crystals so precipitated
  10. filtrationwere filtered off
  11. washwashed with water
  12. customdried
  13. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3a215ff5476f483d9c6c8d1c47eba8e6
Source dataset
uspto-grants-1984_04
Patent number
US04443626

Reaction notes

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