HCID 86740694, compound → HCID 13368792, compound

HRID 483094Notes

Reaction equation

HRID 483094 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:13][C:14]([O:16]C)=O)[C:6]2=[N:11]O.[H][H]>CO.C(O)(=O)C.[Pt]=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]1[CH2:13][C:14](=[O:16])[NH:11][CH:6]12

Participants

6

Reactant 2

HCID 86740694HCID 86740694, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13368792HCID 13368792, compoundYield 40.7%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 4-chloro-1-hydroxyimino-2,3-dihydro-inden-2-acetate (15 g) is hydrogenated at 40 atm of hydrogen in 200 ml of methanol plus 50 ml of acetic acid in the presence of 1.5 g of platinum oxide catalyst at 30°-50° C. for 7 hours. The catalyst is then filtered off, and the filtrate is concentrated. The residual oil is extracted with chloroform. The extract is washed with aqueous potassium carbonate solution, then with water and dried over sodium sulfate, and the solvent is distilled off. The residue is heated on an oil bath at 110°-120° C. for 2 hours. After cooling, ether is added, and the precipitated crystals are collected by filtration and recrystallized from ether to give 5 g of 5-chloro-1,2,3,3a,4,8b-hexahydro-indeno[1,2-b]pyrrol-2-one, melting at 186°-187° C.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated
  3. extractionThe residual oil is extracted with chloroform
  4. washThe extract is washed with aqueous potassium carbonate solution
  5. dry with materialwith water and dried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. temperatureThe residue is heated on an oil bath at 110°-120° C. for 2 hours
  8. temperatureAfter cooling
  9. additionether is added
  10. filtrationthe precipitated crystals are collected by filtration
  11. customrecrystallized from ether

Sources & evidence

ORD record
ord-bbdda0f56589417bb40df59fc165dcda
Source dataset
uspto-grants-1986_03
Patent number
US04578397

Reaction notes

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